Morpholine → 6-(4-ethoxy-3-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246440

반응식

HRID 2246440 반응식
Br[CH2:2][CH2:3][N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=3)[N:9]=[C:8]([C:26]#[N:27])[C:7]=2[N:6]=[CH:5]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CN(C=O)C.CO>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[N:9]=[C:8]([C:26]#[N:27])[C:7]3[N:6]=[CH:5][N:4]([CH2:3][CH2:2][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[C:12]=3[CH:11]=2)=[CH:14][C:15]=1[C:22]([F:25])([F:24])[F:23])[CH3:21]

참가 물질

5

반응물 2

HCID 8083MorpholineHCID 589381211-(2-bromo-ethyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

생성물 1

HCID 177471626-(4-ethoxy-3-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile수율 66.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

1-(2-Bromo-ethyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (92 mg, 0.21 mmol) was dissolved in DMF (2 ml) and morpholine (91 mg, 1.05 mmol) was added. The mixture was heated to 120° C. for 5 minutes in a Smith microwave. Mixture was diluted with methanol (5 ml) and passed through a 5 g SCX cartridge then eluted with 2M methanolic ammonia to afford 62 mg of 6-(4-ethoxy-3-trifluoromethyl-phenyl)-1-(2-morpholin-4-yl-ethyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile as a clear oil. 1H NMR (CDCl3) δ 8.26-8.15 (m, 3H), 7.87 (s, 1H), 7.08 (d, 1H), 4.35 (t, 2H), 4.20 (q, 2H), 3.69 (m, 4H), 2.82 (t, 2H), 2.52 (m, 4H), 1.48 (t, 3H). MS m/z 446.4 (M+1).

후처리

  1. washthen eluted with 2M methanolic ammonia

출처 및 근거

ORD 기록
ord-8bc29b6bde8b405aa22ddb910af88544
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687515B2

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