Ethylamine → HCID 59003296, compound

HRID 2267534Notes

Reaction equation

HRID 2267534 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)=[CH:5][CH:4]=1)=O.[CH2:38]([NH2:40])[CH3:39].[BH4-].[Na+]>CO.C(Cl)Cl>[CH2:38]([NH:40][CH2:1][C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:21][CH2:22][N:23]([S:26]([CH2:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)(=[O:28])=[O:27])[CH2:24][CH2:25]2)=[CH:5][CH:4]=1)[CH3:39]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 59003276HCID 59003276, compound

Product 1

HCID 59003296HCID 59003296, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-(5-formyl-2-thienyl)-3-(1-{[3-(4-morpholinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (20 mg, 0.04 mmol) in MeOH/CH2Cl2 (1 mL/1 mL) was added ethyl amine (0.13 mL, 0.24 mmol). The reaction mixture was stirred at room temperature for 2 hours before NaBH4(10.5 mg, 0.24 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-66502a01932e48f4868ba38471fb4735
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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