2-Butanamine, 2-methyl- → 5-((4-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-N-tert-pentylthiophene-2-carboxamide

HRID 408867Notes

Reaction equation

HRID 408867 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:31])[NH:7][C:8]2[CH:30]=[CH:29][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[S:25][C:24]([C:26]([OH:28])=O)=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[C:41]([NH2:46])([CH2:44][CH3:45])([CH3:43])[CH3:42].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[CH:1]1([CH2:4][NH:5][C:6](=[O:31])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:21]4[S:25][C:24]([C:26]([NH:46][C:41]([CH2:44][CH3:45])([CH3:43])[CH3:42])=[O:28])=[CH:23][CH:22]=4)[CH2:18][CH2:19]3)=[O:13])=[CH:29][CH:30]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 689862-Butanamine, 2-methyl-HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 666616175-((4-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-thiophene-2-carboxylic acid

Product 1

HCID 666612825-((4-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-N-tert-pentylthiophene-2-carboxamideYield 4.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-((4-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)-thiophene-2-carboxylic acid (100 mg, 0.226 mmol), N,N-diisopropylethylamine (99 mg, 0.127 mL, 0.452 mmol) and tert-pentylamine (39 mg, 0.452 mmol) were combined and stirred in dichloromethane. 1-Propanephosphonic acid cyclic anhydride (216 mg, 0.202 mL, 0.339 mmol, 50% solution in ethyl acetate) was added and the reaction stirred for 1 hour at room temperature. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated under vacuum and purified by reverse phase acidic preparative HPLC to afford the title compound (5 mg). MS (ESI) m/z 512.8 [M+H]+

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. custompurified by reverse phase acidic preparative HPLC

Sources & evidence

ORD record
ord-9f3abb6db6134a1795a7841329d5a4b2
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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