Sodium Hydroxide → HCID 57567285、化合物

HRID 74094ノート

反応式

HRID 74094 の反応式
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:14]=1[NH:15][C:16]([C:18]1[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=1)=[O:17])[NH:11][CH:10]=[CH:9]2)=[O:5])C.[OH-].[Na+]>C1COCC1>[O:28]=[C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=[C:18]1[C:16]([NH:15][C:14]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])=[O:17]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 575673926-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid ethyl ester

生成物 1

HCID 57567285HCID 57567285、化合物収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

A mixture of 6-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid ethyl ester (188) (450 mg, 1.2 mmol) and 1N NaOH solution (5 mL) in THF (10 mL) was heated at 85° C. overnight. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was acidified with 1N HCl solution to pH 5, and the precipitate was filtered, washed with water and air dried to yield 6-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid (188-I) (386 mg, 93%). 1H-NMR (400 MHz, DMSO-d6) δ 12.92-12.75 (m, 2H), 11.33 (s, 1H), 8.84 (s, 1H), 8.71 (s, 1H), 8.30 (dd, J=8.1, 0.9 Hz, 1H), 8.22 (s, 1H), 7.80-7.72 (m, 2H), 7.49 (t, J=8.0 Hz, 1H), 7.41 (t, J=2.7 Hz, 1H), 6.51 (m, 1H); HPLC ret. time 2.95 min, 10-99% CH3CN, 5 min run; ESI-MS 376.2 m/z (MH+).

後処理

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. filtrationthe precipitate was filtered
  3. washwashed with water and air
  4. customdried

出典と根拠

ORDレコード
ord-ccd24589aad944cd9c06f1c89bcbf195
出典データセット
uspto-grants-2014_09
特許番号
US08829204B2

反応ノート

読み込み中…