Ethylamine → 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-{3-[(ethylamino) methyl]phenyl}-1H-indole-7-carboxamide

HRID 2267547Notes

Reaction equation

HRID 2267547 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][CH2:5][S:6]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[C:19]([C:32]([NH2:34])=[O:33])[CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=4)[CH:22]=3)[NH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7].[CH2:36]([NH2:38])[CH3:37].C1COCC1.[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:35][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][S:6]([N:9]1[CH2:10][CH2:11][CH:12]([C:15]2[C:23]3[C:18](=[C:19]([C:32]([NH2:34])=[O:33])[CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][NH:38][CH2:36][CH3:37])[CH:25]=4)[CH:22]=3)[NH:17][CH:16]=2)[CH2:13][CH2:14]1)(=[O:8])=[O:7]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 590033553-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 590033053-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-{3-[(ethylamino) methyl]phenyl}-1H-indole-7-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-(3-formylphenyl)-1H-indole-7-carboxamide (25 mg, 0.05 mmol) in MeOH/CH2Cl2 (1 mL/1 mL) was added 2M ethyl amine in THF (0.15 mL, 0.30 mmol). The reaction mixture was stirred at room temperature for 2 hours before NaBH4 (12 mg, 0.3 mmol) was added. The reaction mixture was stirred at room temperature overnight and evaporated all the solvent. The residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to give the title compound (11 mg, 52%)

Workup

  1. additionwas added
  2. customevaporated all the solvent
  3. customThe residue was purified
  4. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-29c20d64a8d94fc9bd1af1c9bc018a14
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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