Diisopropylethylamine → 1-{1-[6-(3-Ethyl-4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 469429Notes

Reaction equation

HRID 469429 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]([C:28]2[CH:39]=[C:38]([CH3:40])[C:31]3[N:32]([CH2:36][CH3:37])[C:33](=[O:35])[O:34][C:30]=3[CH:29]=2)=[O:27])[CH:21]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:36]([N:32]1[C:31]2[C:38]([CH3:40])=[CH:39][C:28]([C:26]([C:22]3[N:23]=[CH:24][N:25]=[C:20]([N:3]4[CH2:4][CH2:5][CH:6]([N:9]5[C:17]6[C:12](=[N:13][CH:14]=[CH:15][CH:16]=6)[NH:11][C:10]5=[O:18])[CH2:7][CH2:8]4)[CH:21]=3)=[O:27])=[CH:29][C:30]=2[O:34][C:33]1=[O:35])[CH3:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 581811956-(6-chloro-pyrimidine-4-carbonyl)-3-ethyl-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 252666211-{1-[6-(3-Ethyl-4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

47 mg (0.20 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one-dihydrochloride, 50 mg (0.20 mmol) 6-(6-chloro-pyrimidine-4-carbonyl)-3-ethyl-4-methyl-3H-benzoxazol-2-one and 0.11 mL (0.64 mmol) DIPEA were combined in 2.0 mL DMF and stirred overnight at RT. The reaction mixture was purified by preparative HPLC. The fractions containing the product were combined, the organic solvent was evaporated down and the residue was neutralised with 1N aqueous sodium hydroxide solution. The precipitate formed was suction filtered, washed with water and dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC
  2. additionThe fractions containing the product
  3. customthe organic solvent was evaporated down
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-072554f7aa5443a59a122006ec7ed5d3
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

Loading…