Trifluoroacetic acid → 6-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetate

HRID 1874835Notes

Reaction equation

HRID 1874835 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[C:23]([NH:28]C(=O)OC(C)(C)C)[CH:22]=3)=[O:18])=[C:11]([F:36])[C:10]=1[O:37][C:38]1[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=1>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:28][C:23]1[CH:22]=[C:21]2[C:26]([CH:27]=[C:19]([C:17]([NH:16][CH2:15][C:12]3[CH:13]=[CH:14][C:9]([Cl:8])=[C:10]([O:37][C:38]4[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=4)[C:11]=3[F:36])=[O:18])[NH:20]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 594515231,1-dimethylethyl (2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-6-yl)carbamate

Product 1

HCID 866448896-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetateYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL, 6.49 mmol) was added to a solution of 1,1-dimethylethyl (2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-6-yl)carbamate (0.046 g, 0.081 mmol) in dichloromethane (2 mL). The mixture was stirred at RT overnight. The solvent was evaporated and the residue was purified by column chromatography (dichloromethane/methanol) to give the title compound (0.037 g, 74%) as a grey solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.73 (s, 1H), 9.35 (br. s., 2H), 9.04 (s, 1H), 7.80 (s, 1H), 7.63 (d, 1H), 7.44-7.54 (m, 3H), 7.38 (t, 1H), 7.27 (s, 1H), 7.17 (s, 1H), 6.88 (d, 1H), 4.55 (d, 2H). MS: m/z 548 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-dd40126d35644513ba028dae8ca88194
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…