Structure of 1032650-41-1
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CAS No. : | 1032650-41-1 |
Formula : | C6H3BrClN3 |
M.W : | 232.47 |
SMILES Code : | ClC1=C(NC=C2Br)C2=NC=N1 |
MDL No. : | MFCD11518977 |
InChI Key : | MSHYYIJDYMVONW-UHFFFAOYSA-N |
Pubchem ID : | 52987660 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.6 |
TPSA ? Topological Polar Surface Area: Calculated from |
41.57 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.67 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.07 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.13 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.89 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.19 |
Solubility | 0.15 mg/ml ; 0.000644 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.57 |
Solubility | 0.623 mg/ml ; 0.00268 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.01 |
Solubility | 0.0225 mg/ml ; 0.0000968 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.25 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.83 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | To a chilled (-780C) solution of 7-bromo-4-chloro-5H-pyrrolo[3,2-?]pyrimidine (80 mg, 0.34 mmol, 1 equiv.) in 5 mL of TetaF was added tert-BwLi (1.7 M in pentane, 0.43 mL, 0.73 mmol, 2.1 equiv.) dropwise. After 5 minutes, a chilled (-780C) solution of 2,2,2-trifluoro-l-[l-(4- fluorophenyl)-lH-indazol-5-yl]ethanone (106 mg, 0.34 mmol, 1 equiv.) in 1 mL of TetaF was added in one portion. After 15 minutes, the reaction was quenched with 15 mL of water, warmed to room temperature, diluted with 100 mL of saturated aqueous ammonium chloride, and then extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was dissolved in DMF and purified by reverse phase etaPLC (5-95% Ceta3Cnu/water +0.1% TFA). The major fractions collected were made basic with saturated NaHCO3 and the CH3CN was concentrated in vacuo. The aqueous was extracted with <n="156"/>EtOAc and washed with brine. The organic layers were dried, filtered, and concentrated in vacuo to provide 52 mg (32%) of the title compound as a white solid. MS m/z 462.56 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | A mixture of 7-bromo-3,5-dihydropyrrolo[3,2-?]pyrimidin-4-one (100 mg, 0.5 mmol) and 6 mL of POCI3 under argon was warmed at 115C. After 3 hours, the mixture was cooled to room temperature and poured over 300 mL of ice, stirred, made basic with potassium carbonate and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 101 mg (93%) of the desired 7-bromo-4-chloro-5H-pyrrolo[3,2- djpyrimidine as beige solid which was used without further purification. | |
90% | With trichlorophosphate; for 2.0h;Inert atmosphere; Reflux; | Under argon atmosphere, a solution of 7-Bromo-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one (500 mg, 2.33 mmol) in phosphorus(V) oxychoride (6 rriL) was refluxed for 2 hours. The reaction mixture was then cooled to room temperature, concentrated and the residue was diluted with ethyl acetate. The organic layer was washed with a solution of sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to afford compound (66a) as a pale solid (490 mg, 2.10 mmol, 90%) without further purification. lH NMR (400 MHz, DMSO-i delta 8.24 (d, J = 3.0 Hz, 1H), 8.72 (s, 1H), 12.95 (bs, 1H). MS m/z ([M+H]+) 232/234 |
35% | With trichlorophosphate; at 115℃; for 3.0h; | Intermediate 98 (1.30 g, 6.07 mmol) was suspended in POCI3 (60 mL) and heated at 115 C for 3 h. The reaction mixture was cooled to r.t. and poured cautiously onto ice (300 mL). The reaction mixture was basified with K2CO3 and extracted with EtOAc (3 x 200 mL). The combined organic fractions were dried (MgS04) and concentrated in vacuo to give the title compound as a beige solid (490 mg, 35%). LCMS (ES+): 231.9, 233.9, 235.9 (M+H)+. |
35% | With trichlorophosphate; at 115℃; for 3.0h; | Intermediate 98 (1.30 g, 6.07 mmol) was suspended in POCl3 (60 mL) and heated at 115 C. for 3 h. The reaction mixture was cooled to r.t. and poured cautiously onto ice (300 mL). The reaction mixture was basified with K2CO3 and extracted with EtOAc (3*200 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid (490 mg, 35%). LCMS (ES+): 231.9, 233.9, 235.9 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In tetrahydrofuran; oil; for 18h; | Step 1 : To Compound 13-1 (0.30g, 1.3mmol) and CH3I (0.12mL, 1.9mmol ) in THF (5mL) was added NaH (60% in oil, 0.078g, 1 ,9mmol). The mixture was stirred 18h and concentrated. | |
romo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine To <strong>[1032650-41-1]7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine</strong> (147 mg), N,N- dimethylformamide (10 mL) was added, and NaH (36 mg) was further added thereto, followed by stirring for 30 min. Subsequently, methyl iodide was added thereto, and the reaction mixture was heated to 50C and stirred for 2 hours. After completion of the reaction, the reaction mixture was mixed with ethyl acetate and washed with water. The washed mixture was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound. 'H NMR (300 MHz, DMSO- 6): delta 8.68(s, 1H), 8.22(s, 1H), 4.11(s, 3H). | ||
To <strong>[1032650-41-1]7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine</strong> (147 mg), N,N-dimethylformamide (10 mL) was added, and NaH (36 mg) was further added thereto, followed by stirring for 30 min. Subsequently, methyl iodide was added thereto, and the reaction mixture was heated to 50 C. and stirred for 2 hours. After completion of the reaction, the reaction mixture was mixed with ethyl acetate and washed with water. The washed mixture was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound. [0214] 1H NMR (300 MHz, DMSO-d6): delta 8.68 (s, 1H), 8.22 (s, 1H), 4.11 (s, 3H). |
Step 4: Preparation of 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine N,N-dimethylformamide (10 mL) and NaH (36 mg) were added to <strong>[1032650-41-1]7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine</strong> (147 mg), followed by stirring for 30 mins. Subsequently, methyl iodide was added thereto, and the mixture was heated under stirring at 50C for 2 hrs. Upon completion of the reaction, ethyl acetate was added thereto, and the mixture was washed with water. The resulting compound was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 8.68(s, 1H), 8.22(s, 1H), 4.11 (s, 3H). | ||
Step 4: Preparation of 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine N,N-dimethylformamide (10 mL) and NaH (36 mg) were added to <strong>[1032650-41-1]7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine</strong> (147 mg), followed by stirring for 30 mins. Subsequently, methyl iodide was added thereto, and the mixture was heated under stirring at 50 C. for 2 hrs. Upon completion of the reaction, ethyl acetate was added thereto, and the mixture was washed with water. The resulting compound was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 8.68 (s, 1H), 8.22 (s, 1H), 4.11 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; In tetrahydrofuran; for 1h; | Step 4-3) 7-bromo-4-chloro-5H-pyrrolo["3,2-dlpyrimidine To 4-chloro-5H-pyrrolo[3,2-i/]pyrimidine (100 mg), tetrahydrofuran (5 mL) was added, and N-bromosuccinimide (116 mg) was further added thereto, followed by stirring for 1 hour. After completion of the reaction, the reaction mixture was mixed with ethyl acetate and washed with water. The washed mixture was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound. 'H NMR (300 MHz, DMSO-i?): delta 12.95 (s, 1 H), 8.71 (s, 1 H), 8.24 (d, 1 H). | |
With N-Bromosuccinimide; In tetrahydrofuran; for 1h; | To 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg), tetrahydrofuran (5 mL) was added, and N-bromosuccinimide (116 mg) was further added thereto, followed by stirring for 1 hour. After completion of the reaction, the reaction mixture was mixed with ethyl acetate and washed with water. The washed mixture was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound. [0211] 1H NMR (300 MHz, DMSO-d6): delta 12.95 (s, 1H), 8.71 (s, 1H), 8.24 (d, 1H) | |
With N-Bromosuccinimide; In tetrahydrofuran; for 1h; | Step 3: Preparation of 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Tetrahydrofuran (5 mL) and N-bromosuccinimide (116 mg) were added to 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg). The mixture was stirred for 1 hr and, upon completion of the reaction, ethyl acetate was added thereto, and washed with water. The mixture was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 12.95 (s, 1 H), 8.71 (s, 1 H), 8.24 (d, 1 H) |
With N-Bromosuccinimide; In tetrahydrofuran; for 1h; | Step 3: Preparation of 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Tetrahydrofuran (5 mL) and N-bromosuccinimide (116 mg) were added to 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg). The mixture was stirred for 1 hr and, upon completion of the reaction, ethyl acetate was added thereto, and washed with water. The mixture was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 12.95 (s, 1H), 8.71 (s, 1H), 8.24 (d, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 99 (500 mg, 2.15 mmol) was dissolved in THF (30 mL) and cooled to -78 C. tBuLi (3.39 mL, 1.9 M in pentane, 6.45 mmol) was added drop-wise and the reaction mixture was stirred at -78 C for 5 min. A solution of oxan-4-one (1.08 g, 10.8 mmol) in THF (10 mL) was added and the reaction mixture was stirred at -78 C for 30 min and then warmed to r.t.. The reaction mixture was quenched with water (5 mL) and concentrated in vacuo. The residue was purified by reverse phase column chromatography to give the crude title compound as a yellow solid (507 mg, 100%).LCMS (ES+): 236.0 (M+H)+. | ||
Intermediate 99 (500 mg, 2.15 mmol) was dissolved in THF (30 mL) and cooled to -78 C. tBuLi (3.39 mL, 1.9 M in pentane, 6.45 mmol) was added drop-wise and the reaction mixture was stirred at -78 C. for 5 min. A solution of oxan-4-one (1.08 g, 10.8 mmol) in THF (10 mL) was added and the reaction mixture was stirred at -78 C. for 30 min and then warmed to r.t. The reaction mixture was quenched with water (5 mL) and concentrated in vacuo. The residue was purified by reverse phase column chromatography to give the crude title compound as a yellow solid (507 mg, 100%). LCMS (ES+): 236.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; In tetrahydrofuran; for 18h; | Example 13Step 1 : To Compound 13-1 (0.50g, 2.2mmol) in THF (15mL) were added di-t-butyl dicarbonate (0.56g, 2.6mmol) and 4-(dimethylamino)pyridine.(0.026g, 0.21mmol). The mixture was stirred 18h and concentrated to provide crude Compound 13-2. |
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