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

HRID 469389Notes

Reaction equation

HRID 469389 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]=[C:22]([CH3:24])[N:21]=[C:20]([C:25]([C:27]2[CH:37]=[C:36]([CH3:38])[C:30]3[N:31]([CH3:35])[C:32](=[O:34])[O:33][C:29]=3[CH:28]=2)=[O:26])[CH:19]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:35][N:31]1[C:30]2[C:36]([CH3:38])=[CH:37][C:27]([C:25]([C:20]3[N:21]=[C:22]([CH3:24])[N:23]=[C:18]([N:1]4[CH2:2][CH2:3][CH:4]([N:7]5[C:15]6[C:10](=[N:11][CH:12]=[CH:13][CH:14]=6)[NH:9][C:8]5=[O:16])[CH2:5][CH2:6]4)[CH:19]=3)=[O:26])=[CH:28][C:29]=2[O:33][C:32]1=[O:34]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 581811376-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 252694571-{1-[6-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-methyl-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

65 mg (0.30 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 95 mg (0.30 mmol) 6-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.11 mL (0.60 mmol) DIPEA were stirred overnight in 3 mL DMF at RT. Then the reaction mixture was purified by preparative HPLC-MS. The fractions containing the product were combined and the organic solvent was evaporated down i. vac. The residue was neutralised with 4N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried.

Workup

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

Sources & evidence

ORD record
ord-8f4cd6b606c64f2f82b209f5a33c2109
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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