Potassium Carbonate → 1-{1-[6-(4-Methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylamino)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 1846522Notes

Reaction equation

HRID 1846522 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]2[CH:34]=[C:33]([CH3:35])[C:28]3[NH:29][C:30](=[O:32])[O:31][C:27]=3[CH:26]=2)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.CN(C=O)C>[CH3:35][C:33]1[C:28]2[NH:29][C:30](=[O:32])[O:31][C:27]=2[CH:26]=[C:25]([NH:24][C:20]2[N:21]=[CH:22][N:23]=[C:18]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[C:15]5[C:10](=[N:11][CH:12]=[CH:13][CH:14]=5)[NH:9][C:8]4=[O:16])[CH2:5][CH2:6]3)[CH:19]=2)[CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22293182Bms-973013HCID 866638946-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 462441461-{1-[6-(4-Methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylamino)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

276 mg (1.26 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 350 mg (0.987 mmol) 6-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one and 350 mg (2.53 mmol) potassium carbonate in 2 mL NMP were stirred for 2 h at 130° C. After cooling to RT the reaction mixture was diluted with DMF and purified by preparative HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. custompurified by preparative HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-badfc32f03b744ed9f621061a62a748a
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

Loading…