Methanol → HCID 86631022, compound

HRID 1806256Notes

Reaction equation

HRID 1806256 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:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[F:32][C:33]([F:37])([F:36])[CH2:34][NH2:35].[BH4-].[Na+].[CH3:40][OH:41]>ClCCl.C(O)(=O)C>[F:32][C:33]([F:37])([F:36])[C:40]([OH:4])=[O:41].[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH:35][CH2:34][C:33]([F:37])([F:36])[F:32])[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 4311764Sodium borohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 86631022HCID 86631022, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (40 mg, 0.09 mmol) and 2,2,2-trifluoroethylamine (78 μL, 0.55 mmol) in dichloromethane (2 mL) and methanol (1 mL) was added 2 drops of acetic acid. The mixture was then stirred overnight. Sodium borohydride (20.8 mg, 0.55 mmol) was then added and the mixture was stirred for 30 min. The resulting mixture was concentrated and dissolved in dimethyl sulfoxide followed by purification by Gilson Preparatory HPLC to give 29.4 mg of the title compound (62.5%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. concentrationThe resulting mixture was concentrated
  3. dissolutiondissolved in dimethyl sulfoxide
  4. customfollowed by purification by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-1944e3a134bb4c4487fb921feba19211
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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