1,2-Dichloroethane → N-((4,6-Dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxamide

HRID 62317

반응식

HRID 62317 반응식
[CH3:1][CH:2]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[C:8]([C:17](O)=[O:18])[C:7]=2[CH:6]=[CH:5]1)[CH3:3].[NH2:20][CH2:21][C:22]1[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:28][C:27]1[CH:26]=[C:25]([CH3:29])[NH:24][C:23](=[O:30])[C:22]=1[CH2:21][NH:20][C:17]([C:8]1[C:7]2[CH:6]=[CH:5][N:4]([CH:2]([CH3:3])[CH3:1])[C:12]=2[CH:11]=[C:10]([C:13]([F:15])([F:16])[F:14])[CH:9]=1)=[O:18]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 674642241-Isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxylic acid

생성물 1

HCID 67468150N-((4,6-Dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxamide수율 65.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 1-(1-methylethyl)-6-(trifluoromethyl)-1H-indole-4-carboxylic acid (40 mg, 0.147 mmol) in dimethyl sulfoxide (1 mL) were added 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (41.7 mg, 0.221 mmol), N-methylmorpholine (0.065 mL, 0.590 mmol), 1-hydroxy-7-azabenzotriazole (40.1 mg, 0.295 mmol) and EDC (56.5 mg, 0.295 mmol), and the mixture was stirred overnight. The mixture was quenched with water (5 mL) and stirred for 10 min. The precipitate was collected by filtration and dried under high vacuum to give the title compound (39 mg, 63%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (m, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 4.36 (d, J=5.05 Hz, 2H), 4.99 (dt, J=13.20, 6.66 Hz, 1H), 5.89 (s, 1H), 6.98 (d, J=3.03 Hz, 1H), 7.68 (s, 1H), 7.86 (d, J=3.28 Hz, 1H), 8.08 (s, 1H), 8.45 (t, J=4.93 Hz, 1H), 11.56 (s, 1H). MS: (M+H)+=406.1.

후처리

  1. customThe mixture was quenched with water (5 mL)
  2. stirringstirred for 10 min
  3. filtrationThe precipitate was collected by filtration
  4. customdried under high vacuum

출처 및 근거

ORD 기록
ord-e49beb8c51ea4fe2bfb63a768d9fd1cc
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446041B2

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