Cesium carbonate → 4-(1-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)piperazin-2-one

HRID 1043606Notes

Reaction equation

HRID 1043606 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:16][CH:15]([N:17]4[CH2:22][CH2:21][NH:20][C:19](=[O:23])[CH2:18]4)[CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:30]([C:32]1[NH:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1)[CH3:31].CC(C)([O-])C.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:30]([C:32]1[N:33]([C:2]2[N:3]=[C:4]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:5]3[N:11]=[C:10]([CH2:12][N:13]4[CH2:14][CH:15]([N:17]5[CH2:22][CH2:21][NH:20][C:19](=[O:23])[CH2:18]5)[CH2:16]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1)[CH3:31]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 158072-EthylbenzimidazoleHCID 23676156Sodium t-butoxideHCID 584050214-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)piperazin-2-one

Product 1

HCID 533785704-(1-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)piperazin-2-one

Procedure

4-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)piperazin-2-one from Example 127 (90 mg) was reacted with 2-ethylbenzimidazole and sodium-tert-butoxide (instead of cesium carbonate) via General Procedure C to afford 10.2 mg of 134 following reverse phase HPLC purification. MS (Q1) 528.3 (M)+

Workup

  1. customto afford
  2. custom10.2 mg of 134 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-683c997ece4341f2ac000590c273189c
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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