Cyclopropanemethanamine → N-Cyclopropylmethyl-4-(3-isopropyl-indole-1-sulfonyl)-benzamide

HRID 737063Notes

Reaction equation

HRID 737063 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:5]=1)([CH3:3])[CH3:2].C1CN([P+](ON2N=[N:49][C:44]3[CH:45]=[CH:46][CH:47]=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1(CN)CC1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:45]1([CH2:44][NH:49][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([S:13]([N:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5]3)(=[O:14])=[O:15])=[CH:17][CH:18]=2)[CH2:47][CH2:46]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58975120HCID 58975120, compound

Product 1

HCID 58975017N-Cyclopropylmethyl-4-(3-isopropyl-indole-1-sulfonyl)-benzamideYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir mixture of 4-(3-isopropyl-indole-1-sulfonyl)-benzoic acid (0.181 g, 0.53 mmol), PyBOP (0.243 g, 0.55 mmol) and cyclopropylmethyl amine (0.064 g, 0.59 mmol) in CH2Cl2 (20 mL) add Hunigs base (0.28 mL, 1.62 mmol) under N2. Stir the resulting mixture overnight at ambient temperature. Extract the reaction with H2O, wash with brine dry (MgSO4), filter, evaporate and chromatograph using hexane-EtOAc (0-100%) to give 0.183 g of the title compound as an off white solid: Mass spectrum (m/e) (M+H) 397.1593; found 397.1586.

Workup

  1. stirringStir the resulting mixture overnight at ambient temperature
  2. extractionExtract
  3. customthe reaction with H2O
  4. washwash with brine
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. customevaporate

Sources & evidence

ORD record
ord-a01292e7c9d24f989f28b9efe78d54eb
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…