Diisopropylethylamine → 3,4-dimethyl-6-{6-[4-(5-oxo-3-phenyl-4,5-dihydro-[1,2,4]triazol-1-yl)-piperidin-1-yl]-pyrimidine-4-carbonyl}-3H-benzoxazol-2-one

HRID 469413Notes

Reaction equation

HRID 469413 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:18])[N:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH: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[CH:21]=[C:20]([N:15]4[CH2:14][CH2:13][CH:12]([N:10]5[C:9](=[O:18])[NH:8][C:7]([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)=[N:11]5)[CH2:17][CH2:16]4)[N:25]=[CH:24][N:23]=3)=[O:27])=[CH:29][C:30]=2[O:34][C:33]1=[O:35]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-oneHCID 1356275985-Phenyl-2-piperidin-4-YL-2,4-dihydro-[1,2,4]triazol-3-one

Product 1

HCID 1359215433,4-dimethyl-6-{6-[4-(5-oxo-3-phenyl-4,5-dihydro-[1,2,4]triazol-1-yl)-piperidin-1-yl]-pyrimidine-4-carbonyl}-3H-benzoxazol-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

98 mg (0.40 mmol) 5-phenyl-2-piperidin-4-yl-2,4-dihydro-[1,2,4]triazol-3-one, 0.12 g (0.40 mmol) 6-(6-chloro-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.14 mL (0.80 mmol) DIPEA were combined in 3 mL DMF and stirred for 48 h at RT. The mixture was diluted with MeOH, suction filtered, washed with MeOH and diethyl ether and dried.

Workup

  1. filtrationfiltered
  2. washwashed with MeOH and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-fb44224501dd40d4939aac573a554b05
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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