Pyrrolidine → 3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-5-[5-(1-pyrrolidinylmethyl)-3-thienyl]-1H-indole-7-carboxamide

HRID 2267590Notes

Reaction equation

HRID 2267590 reaction equation
[CH:1]([C:3]1[S:7][CH:6]=[C:5]([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][O:32][CH3:33])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH:4]=1)=O.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[BH4-].[Na+]>ClCCl.CO.C(O)(=O)C>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][S:26]([N:23]1[CH2:24][CH2:25][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:5]4[CH:4]=[C:3]([CH2:1][N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[S:7][CH:6]=4)[CH:9]=3)[NH:13][CH:12]=2)[CH2:21][CH2:22]1)(=[O:27])=[O:28]

Participants

7

Reactant 3

HCID 31268PyrrolidineHCID 4311764Sodium borohydrideHCID 116201055-(5-formyl-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 590033343-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-5-[5-(1-pyrrolidinylmethyl)-3-thienyl]-1H-indole-7-carboxamideYield 15%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 5-(5-formyl-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (40 mg, 0.08 mmol) in a mixture of dichloromethane (1.25 mL) and methanol (0.5 mL), pyrrolidine (0.07 mL, 0.8 mmol) and 2 drops of acetic acid were added. After the reaction mixture was stirred at room temperature for 6 hours, NaBH4 (30.26 mg, 0.8 mmol) was added. Then the reaction mixture was stirred at room temperature for 30 minutes. All the solvent was evaporated and purified by Gilson HPLC (CH3CN/Water, 0.1% TFA) to give title compound (6.5 mg, 15%).

Workup

  1. additionwere added
  2. stirringThen the reaction mixture was stirred at room temperature for 30 minutes
  3. customAll the solvent was evaporated
  4. custompurified by Gilson HPLC (CH3CN/Water, 0.1% TFA)

Sources & evidence

ORD record
ord-adc9a566de2e4c3ab7fd10f75b0a415e
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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