Diisopropylethylamine → 3-{1-[6-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469394Notes

Reaction equation

HRID 469394 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[NH:9][C:8]2=[O:18])[CH2:3][CH2:2]1.Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]([C:28]2[CH:38]=[C:37]([CH3:39])[C:31]3[N:32]([CH3:36])[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.CO>[CH3:36][N:32]1[C:31]2[C:37]([CH3:39])=[CH:38][C:28]([C:26]([C:22]3[N:23]=[CH:24][N:25]=[C:20]([N:1]4[CH2:2][CH2:3][CH:4]([N:7]5[CH2:13][CH2:12][C:11]6[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=6[NH:9][C:8]5=[O:18])[CH2:5][CH2:6]4)[CH:21]=3)=[O:27])=[CH:29][C:30]=2[O:34][C:33]1=[O:35]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 581811103-{1-[6-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

98 mg (0.40 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 0.12 g (0.40 mmol) 6-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.14 mL (0.80 mmol) DIPEA were stirred in 3 mL DMF for 2 h at RT. The mixture was diluted with methanol, and the precipitate formed was suction filtered, washed with MeOH and diethyl ether and dried.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. washwashed with MeOH and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-9eee556de83b418cbf9d23b3ca3114d7
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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