Water → Dimethyl-(4-{1-methyl-3-[4-(quinolin-2-ylmethoxy)-phenyl]-1H-pyrazol-4-yl}-pyridin-2-yl)-amine

HRID 1170312노트

반응식

HRID 1170312 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[CH:16][CH:15]=3)=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[NH:32]([CH2:36]CO)[CH2:33]CO.O>CN(C)C=O>[CH3:33][N:32]([CH3:36])[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[CH:16][CH:15]=3)=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 8113DiethanolamineHCID 115536722-[4-[4-(2-Chloro-pyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline

생성물 1

HCID 11683518Dimethyl-(4-{1-methyl-3-[4-(quinolin-2-ylmethoxy)-phenyl]-1H-pyrazol-4-yl}-pyridin-2-yl)-amine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

To a solution of 2-{4-[4-(2-Chloro-pyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline (100 mg) in dimethyl formamide (1 ml) was added diethanolamine (0.035 ml) and the reaction mixture heated at 130° C. for 72 h. The reaction mixture was poured into water and extracted with ethyl ether, dried magnesium sulfate, filtered and concentrated. Prep TLC eluting with 60% ethyl acetate/hexane provided the title compound as a Free base. The product was stirred in ethyl acetate and 1 eq. of succinic acid was added. After 18 h, the white precipitate was filtered to provide the succinate salt (24 mg). 1H NMR (400 MHz, DMSO) δ 8.40 (d, J=8.3 Hz, 1H), 8.03 (s, 1H), 7.98 (m, 2H), 7.90 (d, J=5.4 Hz, 1H), 7.77 (m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.59 (m, 1H), 7.31 (d, J=6.6 Hz, 2H), 7.04 (d, J=9.1 Hz, 2H), 6.37 (m, 2H), 5.35 (s, 2H), 3.84 (s, 3H), 2.80 (s, 6H) 2.37 (s, 4H); MS: (M+H m/z=436.0).

후처리

  1. extractionextracted with ethyl ether, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washPrep TLC eluting with 60% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-22a85e4c42984b27a59781018e1172dd
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825254B2

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