(6-Aminopyridin-3-yl)boronic acid → 2-(4-((2-(6-Aminopyridin-3-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-methylpropanamide

HRID 1043592Notes

Reaction equation

HRID 1043592 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]([CH3:24])([CH3:23])[C:20]([NH2:22])=[O:21])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][N:33]=1>>[NH2:31][C:32]1[N:33]=[CH:34][C:35]([C:2]2[N:3]=[C:4]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:5]3[N:11]=[C:10]([CH2:12][N:13]4[CH2:18][CH2:17][N:16]([C:19]([CH3:24])([CH3:23])[C:20]([NH2:22])=[O:21])[CH2:15][CH2:14]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 22396308(6-Aminopyridin-3-yl)boronic acidHCID 584049422-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-methylpropanamide

Product 1

HCID 533784682-(4-((2-(6-Aminopyridin-3-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-methylpropanamide

Procedure

2-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-methylpropanamide from Example 121 (115 mg) was reacted with 2-aminopyridine-5-boronic acid, pinacol ester via General Procedure A to yield 8.5 mg 124 following reverse phase HPLC purification. MS (Q1) 492.3 (M)+

Workup

  1. customto yield
  2. custom8.5 mg 124 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-06d15d18f6734c198cda158edda42df7
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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