N,N-Dimethyl-1H-benzimidazol-2-amine → N,N-dimethyl-1-(4-morpholino-6-((3-morpholinoazetidin-1-yl)methyl)pyrido[3,2-d]pyrimidin-2-yl)-1H-benzo[d]imidazol-2-amine

HRID 1043648Notes

Reaction equation

HRID 1043648 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:16][CH:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:29][N:30]([CH3:40])[C:31]1[NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[N:32]=1>>[CH3:29][N:30]([CH3:40])[C:31]1[N:32]([C:2]2[N:3]=[C:4]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:5]3[N:11]=[C:10]([CH2:12][N:13]4[CH2:14][CH:15]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)[CH2:16]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1

Participants

3

Reactant 2

HCID 17846N,N-Dimethyl-1H-benzimidazol-2-amineHCID 584050304-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine

Product 1

HCID 53377617N,N-dimethyl-1-(4-morpholino-6-((3-morpholinoazetidin-1-yl)methyl)pyrido[3,2-d]pyrimidin-2-yl)-1H-benzo[d]imidazol-2-amine

Procedure

4-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine from Example 126 (75 mg) was reacted with N,N-dimethyl-1H-benzo[d]imidazol-2-amine via General Procedure D to produce 6.8 mg of 167 following reverse phase HPLC purification. MS (Q1) 530.2 (M)+

Workup

  1. customto produce
  2. custom6.8 mg of 167 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-250134cf7fdd490080a7416799f26da8
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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