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

HRID 1806491Notes

Reaction equation

HRID 1806491 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-3e1115b9f4284065a47822ace65d9d32
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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