N,N-Dimethyl-1H-benzimidazol-2-amine → 1-(4-((2-(2-(dimethylamino)-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone

HRID 1043646Notes

Reaction equation

HRID 1043646 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:11]=[C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:28][N:29]([CH3:39])[C:30]1[NH:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[N:31]=1>>[CH3:28][N:29]([CH3:39])[C:30]1[N:31]([C:2]2[N:3]=[C:4]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[C:5]3[N:11]=[C:10]([CH2:12][CH:13]4[CH2:14][CH2:15][N:16]([C:19](=[O:21])[CH3:20])[CH2:17][CH2:18]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1

Participants

3

Reactant 2

HCID 17846N,N-Dimethyl-1H-benzimidazol-2-amineHCID 584049991-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone

Product 1

HCID 533792421-(4-((2-(2-(dimethylamino)-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone

Procedure

1-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone from Example 148 (0.125 g) was reacted with N,N-dimethyl-1H-benzo[d]imidazol-2-amine via General Procedure D to produce 47.5 mg of 165 following reverse phase HPLC purification. MS (Q1) 515.2 (M)+

Workup

  1. customto produce
  2. custom47.5 mg of 165 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-9aa0308b122948588fece0e5f658779a
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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