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

HRID 410189Notes

Reaction equation

HRID 410189 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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) +++++.

Workup

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

Sources & evidence

ORD record
ord-4628dd26814244e7a495b68c5455ec1c
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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