3-Cyanopyridine → 2-Phenyl-5-(2-(pyridin-3-yl)-1h-imidazol-5-yl)pyrimidine

HRID 42281

반응식

HRID 42281 반응식
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)#[N:20].B(O)(O)[C:28]1[CH:33]=CC=[C:30](F)[CH:29]=1>ClCCl.CO>[C:25]1([C:24]2[N:20]=[CH:19][C:21]([C:12]3[NH:8][C:9]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)=[N:10][CH:11]=3)=[CH:22][N:23]=2)[CH:26]=[CH:30][CH:29]=[CH:28][CH:33]=1.[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 793-CyanopyridineHCID 27339863-Fluorophenylboronic acidHCID 673615683-(1-benzyl-1H-imidazol-2-yl)pyridine

생성물 2

HCID 451375612-Phenyl-5-(2-(pyridin-3-yl)-1h-imidazol-5-yl)pyrimidineHCID 673615683-(1-benzyl-1H-imidazol-2-yl)pyridine

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

The title compound was prepared by the method described in Example 1, except that 3-(1-benzyl-1H-imidazol-2-yl)pyridine was used instead of 1-benzyl-2-phenyl-1H-imidazole in Step C. 3-(1-Benzyl-1H-imidazol-2-yl)pyridine was prepared by the method described in Example 8, Steps A and B except the commercially available 3-cyanopyridine was used instead of 3-fluorobenzonitrile; Rf 0.25 with 95:5 v/v dichloromethane-methanol; melting point 308° C; 1H-NMR (400 MHz; DMSO-d6) δ 9.32 (s, 2H), 9.20 (d, 1H), 8.58 (dd, 1H), 8.44-8.31 (m, 3H), 8.12 (m, 1H), 7.57-7.46 (m, 4H); MS (ESI+) m/z 300.1 (M+1); H-PGDS FPBA IC50: 0.079 μM; H-PGDS inhibitor EIA IC50: 0.021 μM.

출처 및 근거

ORD 기록
ord-4d2fcb8da0d046818c6484d02419b0b8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536185B2

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