Trifluoroacetic acid → N-(3-bromo-1,2,4-thiadiazol-5-yl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-1H-indole-6-sulfonamide

HRID 1524436ノート

反応式

HRID 1524436 の反応式
[Br:1][C:2]1[N:6]=[C:5]([N:7](CC2C=CC(OC)=CC=2)[S:8]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=4[C:31]4[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=4)=[CH:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[S:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[N:6]=[C:5]([NH:7][S:8]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][C:22]=4[C:31]4[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=4)=[CH:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)(=[O:9])=[O:10])[S:4][N:3]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 71259358N-(3-bromo-1,2,4-thiadiazol-5-yl)-N-(4-methoxybenzyl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-1H-indole-6-sulfonamide

生成物 1

HCID 71263830N-(3-bromo-1,2,4-thiadiazol-5-yl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-1H-indole-6-sulfonamide収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A 10-mL round-bottom flask was charged with N-(3-bromo-1,2,4-thiadiazol-5-yl)-N-(4-methoxybenzyl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-1H-indole-6-sulfonamide (28 mg, 0.039 mmol), DCM (1 mL), and trifluoroacetic acid (60.1 μl, 0.780 mmol). The flask was sealed, and the mixture was stirred for 2.5 h. An additional portion of TFA (0.15 mL) was added, and the resulting mixture was stirred for 48 h. The volatiles were removed in vacuo, and the residue was concentrated again from DCM. The crude product was purified by chromatography on silica gel (5 to 10% MeOH/DCM) to give N-(3-bromo-1,2,4-thiadiazol-5-yl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-1H-indole-6-sulfonamide (19.91 mg, 0.033 mmol, 85% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=7.94-7.83 (m, 3 H), 7.75 (s, 1 H), 7.55 (d, J=8.5 Hz, 1 H), 7.46-7.35 (m, 2 H), 7.05 (s, 1 H), 6.36 (d, J=1.9 Hz, 1 H), 3.78 (s, 3 H), 3.21 (s, 3 H). m/z (ESI) 597.0 (M+H)+.

後処理

  1. customThe flask was sealed
  2. stirringthe resulting mixture was stirred for 48 h
  3. customThe volatiles were removed in vacuo
  4. concentrationthe residue was concentrated again from DCM
  5. customThe crude product was purified by chromatography on silica gel (5 to 10% MeOH/DCM)

出典と根拠

ORDレコード
ord-e25ed040420741b489602b11b12f489a
出典データセット
uspto-grants-2015_07
特許番号
US09079902B2

反応ノート

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