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[ CAS No. 1408074-49-6 ] {[proInfo.proName]}

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Chemical Structure| 1408074-49-6
Chemical Structure| 1408074-49-6
Structure of 1408074-49-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1408074-49-6 ]

CAS No. :1408074-49-6 MDL No. :MFCD22415180
Formula : C5H12ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 137.61 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 1408074-49-6 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 1408074-49-6 ]

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:

Application In Synthesis of [ 1408074-49-6 ]

* 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.

  • Downstream synthetic route of [ 1408074-49-6 ]

[ 1408074-49-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1408074-49-6 ]
  • [ 2808310-17-8 ]
  • [ 2808310-00-9 ]
YieldReaction ConditionsOperation 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).
  • 2
  • [ 1408074-49-6 ]
  • [ 2808310-21-4 ]
  • [ 2808310-01-0 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 1408074-49-6 ]
  • [ 2446486-53-7 ]
  • [ 2808310-22-5 ]
YieldReaction ConditionsOperation 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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