4-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide Hydrochloride → 3-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)-2-methylpropanoic acid

HRID 527447노트

반응식

HRID 527447 반응식
[CH3:1][CH:2]([CH2:6][C:7](=O)[CH2:8][CH3:9])[C:3]([OH:5])=[O:4].Cl.[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([N:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)N)=[O:18])=[CH:15][CH:14]=1>C(O)(=O)C>[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([N:19]2[C:21]3[C:22](=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[C:8]([CH3:9])=[C:7]2[CH2:6][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[O:18])=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 124352824-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide HydrochlorideHCID 129854572-Methyl-4-oxohexanoic acid

생성물 1

HCID 716008183-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)-2-methylpropanoic acid수율 44%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

2-methyl-4-oxohexanoic acid (27.6 mg, 0.19 mmol) was added to a stirred solution of 4-chloro-N-(4-methoxyphenyl)benzohydrazide hydrochloride (50 mg, 0.16 mmol) in acetic acid (0.5 mL), the mixture was heated at 80° C. under nitrogen for 3 h, then it was allowed to cool to ambient temperature and stirred overnight. Ice-water (2 mL) was poured into the cold reaction mixture and the formed precipitate was collected by filtration, carefully washed with water and dried in vacuo to yield the title compound (27 mg, 44%) as an off-white solid. C21H20ClNO4, Mr=385.84; 1H NMR (400 MHz, DMSO-d6) d: 1.01 (d, J=6.8 Hz, 3H), 2.19 (s, 3H), 2.54 (sex, J=7.2 Hz, 1H), 2.91-3.19 (m, 2H), 3.76 (s, 3H), 6.46 (d, J=9.2 Hz, 1H), 6.64 (dd, J=2.4/9.0 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H); LCMS (ESI) tR: 2.78 min (>99%, ELSD), m/z: 386.1 [M+1]+.

후처리

  1. temperatureto cool to ambient temperature
  2. filtrationthe formed precipitate was collected by filtration
  3. washcarefully washed with water
  4. customdried in vacuo

출처 및 근거

ORD 기록
ord-adfe4f51a13d4a58b4fd4e3818a5a46e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346803B2

반응 노트

불러오는 중…