Morpholine → 1-methyl-N-(4-(3-(morpholinomethyl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

HRID 410189노트

반응식

HRID 410189 반응식
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH:11][C:12]1[CH:26]=[CH:25][C:15]([O:16][C:17]2[N:24]=[CH:23][CH:22]=[CH:21][C:18]=2[CH:19]=O)=[CH:14][CH:13]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[C:18]([CH2:19][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:21][CH:22]=[CH:23][N:24]=2)=[CH:25][CH:26]=1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 593272522-(4-(1-Methyl-1H-benzo[D]imidazol-2-ylamino)phenoxy)nicotinaldehyde

생성물 1

HCID 462153761-methyl-N-(4-(3-(morpholinomethyl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 2-(4-(1-methyl-1H-benzo[d]imidazol-2-ylamino)phenoxy)nicotinaldehyde (0.2 g, 0.6 mmol) in DCM (2 mL) was added morpholine (0.05 mL, 0.6 mmol). Sodium triacetoxyborohydride (0.1 g, 0.6 mmol) was added and the resulting mixture was stirred for 3 h at RT. LC/MS showed complete conversion. The reaction mixture was purified by silica gel chromatography (0-10% MeOH/DCM) to afford product 1-methyl-N-(4-(3-(morpholinomethyl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine as solid. MS (ESI, pos. ion) m/z: 416.1 (M+1). IC50 (uM) +++++.

후처리

  1. customThe reaction mixture was purified by silica gel chromatography (0-10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-4628dd26814244e7a495b68c5455ec1c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

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