6-bromo-N,N-dimethylpyridin-2-amine → 4-((6-(dimethylamino)pyridin-2-yl)(hydroxy)(pyridin-2-yl)methyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773752Notes

Reaction equation

HRID 1773752 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:17]([OH:31])([C:24]3[CH:29]=[CH:28][CH:27]=[C:26](C)[N:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:32])[O:4][N:3]=1.[CH3:33][N:34](C1C=CC=C(Br)N=1)[CH3:35]>>[CH3:33][N:34]([CH3:35])[C:26]1[N:25]=[C:24]([C:17]([OH:31])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:9]2[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:32])[CH:8]=2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 140060626-bromo-N,N-dimethylpyridin-2-amineHCID 862971606-(3,5-dimethylisoxazol-4-yl)-4-(hydroxy(6-methylpyridin-2-yl)(pyridin-2-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 1176019484-((6-(dimethylamino)pyridin-2-yl)(hydroxy)(pyridin-2-yl)methyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Procedure

A procedure similar to that used for 6-(3,5-dimethylisoxazol-4-yl)-4-(hydroxy(6-methylpyridin-2-yl)(pyridin-2-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one, using 6-bromo-2-N,N-dimethylaminopyridine as the starting material was used to produce the intermediate (C32H36N6O5, 585.2 (M+1)), which was taken directly to the deprotection step to yield the title compound as a yellow oil.

Workup

  1. customto produce the intermediate (C32H36N6O5, 585.2 (M+1)), which

Sources & evidence

ORD record
ord-25971bb939fc490280371bcdeb585635
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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