1-amino-3-(1H-1,2,3-triazol-1-yl)propan-2-ol → 2,4-dimethyl-5-[2-oxo-1,2-dihydro-indol-(3Z)-ylidene-methyl]-1H-pyrrole-3-carboxylic acid (2-hydroxy-3-[1,2,3]triazol-1-yl-propyl)-amide

HRID 481053ノート

反応式

HRID 481053 の反応式
[O:1]=[C:2]1[C:10](=[CH:11][C:12]2[NH:16][C:15]([CH3:17])=[C:14]([C:18]([OH:20])=O)[C:13]=2[CH3:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[NH2:22][CH2:23][CH:24]([OH:31])[CH2:25][N:26]1[CH:30]=[CH:29][N:28]=[N:27]1>>[OH:31][CH:24]([CH2:25][N:26]1[CH:30]=[CH:29][N:28]=[N:27]1)[CH2:23][NH:22][C:18]([C:14]1[C:13]([CH3:21])=[C:12](/[CH:11]=[C:10]2\[C:2](=[O:1])[NH:3][C:4]3[C:9]\2=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:16][C:15]=1[CH3:17])=[O:20]

参加物

3

反応物 2

HCID 187656671-amino-3-(1H-1,2,3-triazol-1-yl)propan-2-olHCID 573671715-(2-Oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1h-pyrrole-3-carboxylic acid

生成物 1

HCID 101582422,4-dimethyl-5-[2-oxo-1,2-dihydro-indol-(3Z)-ylidene-methyl]-1H-pyrrole-3-carboxylic acid (2-hydroxy-3-[1,2,3]triazol-1-yl-propyl)-amide

実験手順

5-(2-Oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (113 mg, 0.4 mmol) was condensed with 1-amino-3(1,2,3)triazole-1-yl-propan-2-ol (85 mg, 0.48 mmol) to precipitate 2,4-dimethyl-5-[2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-1H-pyrrole-3-carboxylic acid (2-hydroxy-3-[1,2,3]triazol-1-yl-propyl)-amide (70 mg, 41%). 1H NMR (DMSO-d6) δ2.45, 2.48 (2×s, 6H, 2×CH3), 3.35 (m, 2H), 4.02 (m, 1H), 4.32 (dd, J=7.6, 14 Hz,1H), 4.53 (dd, J=3.4, 14 Hz,1H), 5.43 (d, J=5.6 Hz, 1H, OH), 6.91 (d, J=7.6 Hz, 1H), 7.01 (t, J=7.6 Hz, 1H), 7.15 (t, J=8.0 Hz, 1H), 7.66 (s, 1H), 7.12 (t, J=5.6 Hz, 1H), 7.74 (s, 1H), 7.77 (d, J=7.6 Hz, 1H), 8.11 (s, 1H), 10.93 (s, 1H, CONH), 13.68 (s, 1H, NH). LC-MS (m/z) 405.4 (M−1).

後処理

  1. customto precipitate 2,4-dimethyl-5-[2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-1H-pyrrole-3-carboxylic acid (2-hydroxy-3-[1,2,3]triazol-1-yl-propyl)-amide (70 mg, 41%)

出典と根拠

ORDレコード
ord-3301ed53ee8c400a80f34015bb1c8428
出典データセット
uspto-grants-2003_11
特許番号
US06653308B2

反応ノート

読み込み中…