Diisopropylethylamine → HCID 178510237、化合物

反応式

[NH2:1][CH2:2][C:3]1[C:4]([F:23])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Br:24][C:25]1[N:26]=[CH:27][NH:28][C:29]=1[C:30](O)=[O:31].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:24][C:25]1[N:26]=[CH:27][NH:28][C:29]=1[C:30]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[C:13]([C:14]#[N:15])[CH:12]=2)[C:4]=1[F:23])=[O:31]

参加物

実験手順

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (36.1 mg, 0.105 mmol), 4-bromo-1H-imidazole-5-carboxylic acid (20.0 mg, 0.105 mmol) and diisopropylethyl amine (0.0366 mL, 0.210 mmol) in DMF (5 ml) was added HATU (39.8 mg, 0.105 mmol) and the mixture was stirred at rt for 30 minutes. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-bromo-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (11.0 mg, 0.021 mmol, 20% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.27-8.50 (m, 1H), 8.11 (s, 1H), 7.76-7.89 (m, 2H), 7.74 (s, 1H), 7.50 (dd, 1H), 7.37 (t, 1H), 4.50 (d, 2H). LC-MS (ES+) m/z 516.90, [M+H].

後処理

washwashed with water
customThe solvent was removed
customthe crude material was purified via reverse phase HPLC

出典と根拠

ORDレコード: ord-0c81ce9018f149a09fdf83511dd1fb83
出典データセット: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08304419B2

反応ノート

読み込み中…

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 2

実験手順

後処理

出典と根拠

反応ノート