Methanol → N-((1-(2-(3-tert-butylureido)ethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 1046556Notes

Reaction equation

HRID 1046556 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5]1.[C:28]([N:32]=[C:33]=[O:34])([CH3:31])([CH3:30])[CH3:29].CO>C(Cl)Cl>[C:28]([NH:32][C:33](=[O:34])[NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH2:8][CH2:9]1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 62412tert-Butyl isocyanateHCID 57993201N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 57993133N-((1-(2-(3-tert-butylureido)ethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (25 mg, 0.063 mmol) in CH2Cl2 (1.5 mL) was treated with t-butyl isocyanate (30 mg, 0.13 mmol). The mixture was stirred overnight, treated with MeOH (1 mL). The solvent was removed in vacuo. The residue was purified by HiTOPs.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by HiTOPs

Sources & evidence

ORD record
ord-fef7a1f14596418abb7161e6f734ea32
Source dataset
uspto-grants-2013_10
Patent number
US08569344B2

Reaction notes

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