Methanol → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-1H-indole-7-carboxamide trifluoroacetate

HRID 562308Notes

Reaction equation

HRID 562308 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH:26]=O)[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[F:31][C:32]([F:39])([F:38])[C@@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1.[BH4-].[Na+].[CH3:42][OH:43]>C(Cl)Cl.C(O)(=O)C>[F:31][C:32]([F:39])([F:38])[C:42]([OH:4])=[O:43].[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH2:26][N:34]5[CH2:35][CH2:36][CH2:37][C@H:33]5[C:32]([F:39])([F:38])[F:31])[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:4])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 2782840(2S)-2-(trifluoromethyl)pyrrolidineHCID 4311764Sodium borohydrideHCID 577327033-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 866310363-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-1H-indole-7-carboxamide trifluoroacetateYield 8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (50 mg, 0.112 mmol) in DCM (3.0 mL) and MeOH (1.5 mL) was added (2S)-2-(trifluoromethyl)pyrrolidine (156 mg, 1.12 mmol) and acetic acid (5 drops). After 6 h of stirring at room temperature, sodium borohydride (43 mg, 1.12 mmol) was added and the reaction was stirred overnight at room temperature. The reaction mixture was purified by Gilson Preparatory HPLC to give 5.0 mg of the title compound (8%).

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. customThe reaction mixture was purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-006d9f284bbe4e4e9c2d5c05ca942d37
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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