Sodium Hydroxide → HCID 57567285, 화합물

HRID 74094노트

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HRID 74094 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 57567285HCID 57567285, 화합물수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-ccd24589aad944cd9c06f1c89bcbf195
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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