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CAS No. : | 1408074-49-6 | MDL No. : | MFCD22415180 |
Formula : | C5H12ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 137.61 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 34.79 |
TPSA : | 35.25 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.56 |
Log Po/w (WLOGP) : | 0.92 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 0.25 |
Consensus Log Po/w : | 0.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.98 |
Solubility : | 14.4 mg/ml ; 0.105 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.87 |
Solubility : | 18.5 mg/ml ; 0.134 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.22 |
Solubility : | 83.1 mg/ml ; 0.604 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
32.8% | With N-ethyl-N,N-diisopropylamine In (methylsulfinyl)methane at 100℃; | 1.E Step E: 6-(2-Fluoro-3-methoxyphenyl)-N-((1r,3r)-3-methoxycyclobutyl)-2-(1- methyl-1H-imidazol-2-yl)-5-phenylthieno[2,3-d]pyrimidin-4-amine 40. 4-Chloro-6-(2-fluoro-3-methoxyphenyl)-2-(1-methyl-1H-imidazol-2-yl)-5- phenylthieno[2,3-d]pyrimidine 40d (17.23 mg, 38.21 µmol) was dissolved in DMSO (5 mL) and (1r,3r)-3-methoxycyclobutan-1-amine hydrochloride (5.26 mg, 38.21 µmol) with ethylbis(propan-2-yl)amine (14.84 mg, 114.82 µmol, 20.0 µl, 3.0 equiv) were added. The mixture was heated at 100°C overnight, cooled and purified by HPLC to give 6-(2-fluoro-3- methoxyphenyl)-N-((1r,3r)-3-methoxycyclobutyl)-2-(1-methyl-1H-imidazol-2-yl)-5- phenylthieno[2,3-d]pyrimidin-4-amine 40 (6.8 mg, 32.8% yield).1H NMR (CDCl3, 400 MHz): δ (ppm) 1.26 (m, 2H), 2.79 (m, 2H), 3.16 (s, 3H), 3.70 (t, 1H), 3.82 (s, 3H), 4.30 (s, 3H), 4.75 (m, 1H), 5.04 (m, 1H), 6.73 (t, 1H), 6.86 - 6.91 (m, 2H), 7.10 (m, 1H), 7.31 (m, 2H), 7.41 (m, 3H), 7.49 (m, 1H). |
32.8% | With N-ethyl-N,N-diisopropylamine In (methylsulfinyl)methane at 100℃; | Step E: 6-(2-Fluoro-3-methoxyphenyl)-N-((1r,3r)-3-methoxycyclobutyl)-2-(1- methyl-1H-imidazol-2-yl)-5-phenylthieno[2,3-d]pyrimidin-4-amine 40. 4-Chloro-6-(2-fluoro-3-methoxyphenyl)-2-(1-methyl-1H-imidazol-2-yl)-5- phenylthieno[2,3-d]pyrimidine 40d (17.23 mg, 38.21 µmol) was dissolved in DMSO (5 mL) and (1r,3r)-3-methoxycyclobutan-1-amine hydrochloride (5.26 mg, 38.21 µmol) with ethylbis(propan-2-yl)amine (14.84 mg, 114.82 µmol, 20.0 µl, 3.0 equiv) were added. The mixture was heated at 100°C overnight, cooled and purified by HPLC to give 6-(2-fluoro-3- methoxyphenyl)-N-((1r,3r)-3-methoxycyclobutyl)-2-(1-methyl-1H-imidazol-2-yl)-5- phenylthieno[2,3-d]pyrimidin-4-amine 40 (6.8 mg, 32.8% yield).1H NMR (CDCl3, 400 MHz): δ (ppm) 1.26 (m, 2H), 2.79 (m, 2H), 3.16 (s, 3H), 3.70 (t, 1H), 3.82 (s, 3H), 4.30 (s, 3H), 4.75 (m, 1H), 5.04 (m, 1H), 6.73 (t, 1H), 6.86 - 6.91 (m, 2H), 7.10 (m, 1H), 7.31 (m, 2H), 7.41 (m, 3H), 7.49 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.3% | With N-ethyl-N,N-diisopropylamine In (methylsulfinyl)methane at 100℃; | 1.E Step E: 6-(2-Fluoro-3-methoxyphenyl)-N-((1r,3r)-3-methoxycyclobutyl)-5-methyl-2- (1-methyl-1H-imidazol-2-yl)thieno[2,3-d]pyrimidin-4-amine 42. 4-Chloro-6-(2-fluoro-3-methoxyphenyl)-5-methyl-2-(1-methyl-1H-imidazol-2- yl)thieno[2,3-d]pyrimidine 42d (200.63 mg, 515.95 µmol) was dissolved in DMSO (7 mL) and (1r,3r)-3-methoxycyclobutan-1-amine hydrochloride (106.5 mg, 773.93 µmol) with ethylbis(propan-2-yl)amine (200.34 mg, 1.55 mmol, 270.0 µL, 3.0 equiv) were added at room temperature. The mixture was heated at 100oC overnight, cooled and purified by HPLC (SunFire C18 Column; 2 - 10 min 60 - 75% methanol+NH3; 30 mL/min).6-(2-Fluoro-3-methoxyphenyl)- N-((1r,3r)-3-methoxycyclobutyl)-5-methyl-2-(1-methyl-1H-imidazol-2-yl)thieno[2,3- d]pyrimidin-4-amine 42 was obtained as yellow gum (18.0 mg, 7.3% yield).1H NMR (DMSO- d6, 400 MHz): δ (ppm) 2.30 (m, 4H), 2.50 (s, 3H), 3.18 (s, 3H), 3.93 (s, 3H), 4.05 (m, 4H), 4.71 - 4.77 (m, 1H), 6.85 (d, 1H), 7.03 (m, 2H), 7.28 - 7.32 (m, 3H). |
18 mg | With N-ethyl-N,N-diisopropylamine In (methylsulfinyl)methane at 100℃; | Step E: 6-(2-Fluoro-3-methoxyphenyl)-N-((1r,3r)-3-methoxycyclobutyl)-5-methyl-2- (1-methyl-1H-imidazol-2-yl)thieno[2,3-d]pyrimidin-4-amine 42. 4-Chloro-6-(2-fluoro-3-methoxyphenyl)-5-methyl-2-(1-methyl-1H-imidazol-2- yl)thieno[2,3-d]pyrimidine 42d (200.63 mg, 515.95 µmol) was dissolved in DMSO (7 mL) and (1r,3r)-3-methoxycyclobutan-1-amine hydrochloride (106.5 mg, 773.93 µmol) with ethylbis(propan-2-yl)amine (200.34 mg, 1.55 mmol, 270.0 µL, 3.0 equiv) were added at room temperature. The mixture was heated at 100°C overnight, cooled and purified by HPLC (SunFire C18 Column; 2 - 10 min 60 - 75% methanol+NH3; 30 mL/min).6-(2-Fluoro-3-methoxyphenyl)- N-((1r,3r)-3-methoxycyclobutyl)-5-methyl-2-(1-methyl-1H-imidazol-2-yl)thieno[2,3- d]pyrimidin-4-amine 42 was obtained as yellow gum (18.0 mg, 7.3% yield).1H NMR (DMSO- d6, 400 MHz): δ (ppm) 2.30 (m, 4H), 2.50 (s, 3H), 3.18 (s, 3H), 3.93 (s, 3H), 4.05 (m, 4H), 4.71 - 4.77 (m, 1H), 6.85 (d, 1H), 7.03 (m, 2H), 7.28 - 7.32 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 16h; | 1.D Step D: 6-Bromo-N-((1r,3r)-3-methoxycyclobutyl)-2-(1-methyl-1H-imidazol-2-yl)- 5-phenylthieno[2,3-d]pyrimidin-4-amine 45d. Diisopropylethylamine (717.12 mg, 5.55 mmol) was added in one portion to the solution of 6-bromo-4-chloro-2-(1-methyl-1H-imidazol-2-yl)-5-phenylthieno[2,3-d]pyrimidine 45c (750.0 mg, 1.85 mmol) and (1r,3r)-3-methoxycyclobutan-1-amine hydrochloride (305.41 mg, 2.22 mmol) in DMF (10 mL). The mixture was heated to 100°C and stirred at this temperature for 16 h. The mixture was purified by HPLC (2 - 10 min; 40 - 70% H2O- MeOH+NH3, flow 30 mL/min ((loading pump 4 mL MeOH); column: YMC-ACTUS TRIART C18100*205 microM).6-Bromo-N-((1r,3r)-3-methoxycyclobutyl)-2-(1-methyl-1H-imidazol-2- yl)-5-phenylthieno[2,3-d]pyrimidin-4-amine 45d (200.0 mg, 425.18 µmol, 23% yield) was obtained. |
200.0 mg | With N-ethyl-N,N-diisopropylamine In (methylsulfinyl)methane at 100℃; | Step D: 6-Bromo-N-((1r,3r)-3-methoxycyclobutyl)-2-(1-methyl-1H-imidazol-2-yl)- 5-phenylthieno[2,3-d]pyrimidin-4-amine 45d. Diisopropylethylamine (717.12 mg, 5.55 mmol) was added in one portion to the solution of 6-bromo-4-chloro-2-(1-methyl-1H-imidazol-2-yl)-5-phenylthieno[2,3-d]pyrimidine 45c (750.0 mg, 1.85 mmol) and (1r,3r)-3-methoxycyclobutan-1-amine hydrochloride (305.41 mg, 2.22 mmol) in DMF (10 mL). The mixture was heated to 100°C and stirred at this temperature for 16 h. The mixture was purified by HPLC (2 - 10 min; 40 - 70% H2O- MeOH+NH3, flow 30 mL/min ((loading pump 4 mL MeOH); column: YMC-ACTUS TRIART C18100*205 microM).6-Bromo-N-((1r,3r)-3-methoxycyclobutyl)-2-(1-methyl-1H-imidazol-2- yl)-5-phenylthieno[2,3-d]pyrimidin-4-amine 45d (200.0 mg, 425.18 µmol, 23% yield) was obtained. |
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