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

HRID 1875037노트

반응식

HRID 1875037 반응식
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18]C(=O)OC(C)(C)C)[CH:16]=2)[NH:11][C:10]=1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([O:37][C:38]2[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=2)[C:31]=1[F:47])=[O:27]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([O:37][C:38]3[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=3)[C:31]=1[F:47])=[O:27])=[C:9]2[Cl:8]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 866449121,1-dimethylethyl (3-chloro-2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)carbamate

생성물 1

HCID 866449135-amino-3-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (0.5 mL, 6.49 mmol) was added to a suspension of 1,1-dimethylethyl (3-chloro-2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)carbamate (0.030 g, 0.050 mmol) in dichloromethane (3 mL). The resulting solution was stirred at room temperature overnight. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA) to give the title compound (0.021 g, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.98-12.29 (m, 1H), 8.80-9.68 (m, 2H), 8.53-8.63 (m, 1H), 7.78-7.85 (m, 1H), 7.39-7.57 (m, 5H), 7.31-7.39 (m, 1H), 7.09-7.20 (m, 1H), 4.41-4.89 (m, 2H). ES MS: m/z 503 (M+1).

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA)

출처 및 근거

ORD 기록
ord-2b0802df26ac4e57a1f6d24ffdc899cc
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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