Water → 2,2,2-trichloroethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-ylcarbamate

HRID 1711670노트

반응식

HRID 1711670 반응식
[C:1]([C:5]1[CH:6]=[C:7]([NH2:20])[N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:20][C:28](=[O:29])[O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])[N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 588517633-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amine

생성물 1

HCID 672534002,2,2-trichloroethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-ylcarbamate수율 62.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a cold solution (−10° C.) of 5-tert-butyl-2-quinolin-6-yl-2H-pyrazol-3-ylamine (8.00 g, 30 mmol) in 100 ml of CH2Cl2 was added pyridine (8.0 ml, 99 mmol) and DMAP (100 mg), followed by a solution of trichloroethyl chloroformate (8.9 ml, 42 mmol) in 30 ml of CH2Cl2 over a period of 20 minutes. After stirring for 1 hour, water (100 ml) was added, stirring continued for 10 more minutes and the organic layer separated. The organic layer was washed with brine, dried and the dark brown residue obtained after removal of the solvent crystallized from acetonitrile to furnish 2,2,2-trichloroethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-ylcarbamate as a white solid (8.23 g, 62% yield). 1H NMR (DMSO-d6) δ 10.15 (br s, 1H) 8.93 (m, 1H), 8.41 (d, J=8 Hz, 1H), 8.11 (m, 2H), 7.90 (dd, J=8, 2 Hz, 1H), 7.60 (dd, J=6.4, 4.2 Hz, 1H), 6.39 (s, 1H), 4.85 (s, 2H), 1.32 (s, 9H); MS (ESI) m/z: 442 (M+H+).

후처리

  1. stirringstirring
  2. customthe organic layer separated
  3. washThe organic layer was washed with brine
  4. customdried
  5. customthe dark brown residue obtained
  6. customafter removal of the solvent
  7. customcrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-f4f54752980941a280bd2188df3b5f38
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790756B2

반응 노트

불러오는 중…