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

HRID 1846521Notes

Reaction equation

HRID 1846521 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]([O: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.CCN(C(C)C)C(C)C>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]([O: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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22293182Bms-9730132×HCID 866638916-(6-chloro-pyrimidin-4-yloxy)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 462441451-{1-[6-(4-Methyl-2-oxo-2,3-dihydro-benzoxazol-6-yloxy)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40 mg (0.18 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 50 mg (0.18 mmol) 6-(6-chloro-pyrimidin-4-yloxy)-4-methyl-3H-benzoxazol-2-one and 0.10 mL (0.58 mmol) DIPEA were combined in 1.8 mL DMF and stirred for 1 h at RT. Then another 40 mg (0.18 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo-[4,5-b]pyridin-2-one were added and the mixture was stirred overnight. The reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined, the acetonitrile was evaporated down, the precipitate was suction filtered and dried i. vac.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction mixture was purified by preparative HPLC-MS
  3. customthe acetonitrile was evaporated down
  4. filtrationfiltered
  5. customdried i

Sources & evidence

ORD record
ord-8811d415373e47b484a00da2efad2aba
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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