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

HRID 410189ノート

反応式

HRID 410189 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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) +++++.

後処理

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

出典と根拠

ORDレコード
ord-4628dd26814244e7a495b68c5455ec1c
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

反応ノート

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