Methanol → N-(4-(4-amino-7-(3-hydroxypropyl)thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

HRID 2390750Notes

Reaction equation

HRID 2390750 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]/[CH2:34][OH:35])=[CH:4][N:3]=1.CO.[BH4-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([CH2:32][CH2:33][CH2:34][OH:35])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 18451044trans-N-(4-(4-amino-7-(3-hydroxyprop-1-enyl)thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

Product 1

HCID 18451204N-(4-(4-amino-7-(3-hydroxypropyl)thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-{4-Amino-7-[(1E)-3-hydroxyprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (110 mg, 0.228 mmol), methanol (2 mL) and N,N-dimethylformamide (2 mL) was added sodium borohydride (26.9 mg, 0.684 mmol) under an atmosphere of nitrogen. Mixture stirred for 30 minutes at room temperature after which it was treated with 1M sodium carbonate (5 mL) and extracted with dichloromethane (3×5 mL). The organic layer was separated, dried over magnesium sulfate, and filtered, and the solvent was removed under reduced pressure. The product was purified via flash chromatography to furnish the title compound as a pale yellow powder (21.1 mg, 0.0434 mmol): LCMS (Thermoquest AQA single-quad MS, Genesis C18 column, 3 min particle size, 33×4.6 min; 70% 50 mM ammonium Acetate in Water to 95% Acetonitrile over 4.5 mM, 0.8 mL/min): MH+=487 RT=3.23 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (1H), 7.99 (1H), 7.70 (2H), 7.60 (1H), 7.55 (1H), 7.32-7.35 (2H), 7.21 (1H), 7.15 (1H), 7.07 (1H), 5.34 (2H), 4.04 (3H), 3.91 (3H), 3.47 (2H), 2.75 (2H), 1.83 (4H).

Workup

  1. extractionextracted with dichloromethane (3×5 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe product was purified via flash chromatography

Sources & evidence

ORD record
ord-64fc0cda5054401f954af92956587f63
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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