Sodium borohydride → HCID 18451087, compound

HRID 2390703Notes

Reaction equation

HRID 2390703 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[N:23]([CH3:31])[C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:21])=[C:15]([O:32][CH3:33])[CH:14]=3)=[CH:11][S:12][C:8]=2[C:7]([C:34]2[CH:38]=[CH:37][S:36][C:35]=2[CH:39]=[O:40])=[CH:6][N:5]=1>CN(C)C=O.C(Cl)Cl>[NH2:3][C:4]1[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[N:23]([CH3:31])[C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:21])=[C:15]([O:32][CH3:33])[CH:14]=3)=[CH:11][S:12][C:8]=2[C:7]([C:34]2[CH:38]=[CH:37][S:36][C:35]=2[CH2:39][OH:40])=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18451086N-{4-[4-amino-7-(2-formylthien-3-yl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide

Product 1

HCID 18451087HCID 18451087, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (9.4 mg, 0.223 mmol) was added to a mixture of N-{4-[4-amino-7-(2-formylthien-3-yl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide (40.0 mg, 0.0743 mmol) in N,N-dimethylformamide (5 mL) under an atmosphere of nitrogen gas. The solution was stirred for 20 hours at room temperature after which it was diluted with methylene chloride and was washed with water (10 mL) and brine (10 mL). The organics were dried over magnesium sulfate and the solvent was removed in vacuo. The product was purified via flash chromatography to furnish the title compound as a yellow powder (12.0 mg, 0.0222 mmol). LCMS (Conditions a): (MH+)=541.0, RT=3.70 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (s, 1H), 7.99 (d, J=8.2 Hz, 1H), 7.81 (s, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.60 (d, J=5.1 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.55 (s, 1H), 7.35-7.32 (m, 2H), 7.24 (d, J=5.1 Hz, 1H), 7.21 (d, J=1.56 Hz, 1H), 7.13 (m, 1H), 7.09 (dd, J=8.2, 1.56 Hz, 1H), 5.58 (br, 2H), 4.57 (d, J=5.5 Hz, 2H), 4.02 (s, 3H), 3.90 (s, 3H).

Workup

  1. washwas washed with water (10 mL) and brine (10 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe product was purified via flash chromatography

Sources & evidence

ORD record
ord-27f01bc7e378448d93c006d39bf3fee8
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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