Diethylamine → N-ethylethanaminium 4-{1-[({1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]cyclopropyl}benzoate

HRID 1694385Notes

Reaction equation

HRID 1694385 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:19][C:20]3([C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37].COC(C)(C)C>C(O)C>[F:35][C:2]([F:1])([F:34])[C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:19][C:20]3([C:23]4[CH:24]=[CH:25][C:26]([C:27]([O-:29])=[O:28])=[CH:30][CH:31]=4)[CH2:21][CH2:22]3)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.[CH2:36]([NH2+:38][CH2:39][CH3:40])[CH3:37]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 15413tert-Butyl methyl etherHCID 250030754-(1-(1-(4-(trifluoromethyl)benzyl)-1H-indole-7-carboxamido)cyclopropyl)benzoic acid

Product 1

HCID 67279731N-ethylethanaminium 4-{1-[({1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]cyclopropyl}benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-{1-[({1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]cyclopropyl}benzoic acid (13 g, 27.2 mmol) was dissolved in 146 ml ethanol. Diethylamine (3.4 ml, 33 mmol) was added and the mixture was stirred 30 min (formation of precipitate observed). 260 ml of methyl tert-butylether was added and the mixture aged one hour. The solid was collected by filtration, washed with methyl tert-butylether and dried under vacuum at 85° C. for 24 h. 1H NMR 6 Acetone-d6: 8.30 (1H, s), 7.90 (2H, d), 7.80 (1H, d), 7.55 (2H, d), 7.45-7.35 (4H, m), 7.15 (1H, d), 7.00 (2H, d), 6.70 (1H, d), 5.80 (2H, s), 2.60 (4H, q), 1.25-1.20 (2H, m), 1.10-1.05 (8H, m).

Workup

  1. customthe mixture aged one hour
  2. filtrationThe solid was collected by filtration
  3. washwashed with methyl tert-butylether
  4. customdried under vacuum at 85° C. for 24 h

Sources & evidence

ORD record
ord-99f274b087ce41579f6c2661aa68c990
Source dataset
uspto-grants-2012_04
Patent number
US08158671B2

Reaction notes

Loading…