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

HRID 1874827Notes

Reaction equation

HRID 1874827 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][C:24]([NH:28][C:29]([C@@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2C(OC(C)(C)C)=O)=[O:30])=[CH:23][CH:22]=3)=[O:18])=[C:11]([F:43])[C:10]=1[O:44][C:45]1[CH:50]=[C:49]([C:51]#[N:52])[CH:48]=[C:47]([Cl:53])[CH:46]=1>ClCCl>[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][C:24]([NH:28][C:29](=[O:30])[C@@H:31]2[CH2:35][CH2:34][CH2:33][NH:32]2)=[CH:23][CH:22]=3)=[O:18])=[C:11]([F:43])[C:10]=1[O:44][C:45]1[CH:50]=[C:49]([C:51]#[N:52])[CH:48]=[C:47]([Cl:53])[CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 594514741,1-dimethylethyl(2S)-2-{[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)amino]carbonyl}-1-pyrrolidinecarboxylate

Product 1

HCID 86644886N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-5-(L-prolylamino)-1H-indole-2-carboxamide trifluoroacetateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.25 mL, 3.24 mmol) was added to a suspension of 1,1-dimethylethyl(2S)-2-{[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino}carbonyl]-1H-indol-5-yl)amino]carbonyl}-1-pyrrolidinecarboxylate (0.013 g, 0.020 mmol) in dichloromethane (1 mL). The resulting solution was stirred at RT for 1 h. The solvent was evaporated to give the title compound (0.013 g, 98%) an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.67 (s, 1H), 10.38 (s, 1H), 9.24 (s, 1H), 9.02 (s, 1H), 8.66 (s, 1H), 7.95 (s, 1H), 7.81 (s, 1H), 7.46-7.55 (m, 2H), 7.36-7.44 (m, 1H), 7.28 (dd, 1H), 7.15 (d, 1H), 4.57 (s, 2H), 4.30 (m, 1H), 3.28 (m, 2H), 1.75-2.14 (m, 4H). MS: m/z 566 (M).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-36963b5609db447db92c42e4e342709a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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