Diisopropylethylamine → 3,4-dimethyl-6-(6-(2'-oxo-2',3'-dihydro-1'H-spiro[piperidin-4,4'-quinazolin]-1-yl)pyrimidin-4-carbonyl)benzo[d]oxazol-2(3H)-one

HRID 2096368Notes

Reaction equation

HRID 2096368 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[NH:3][C:2]1=[O:16].Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([C:24]([C:26]2[CH:36]=[C:35]([CH3:37])[C:29]3[N:30]([CH3:34])[C:31](=[O:33])[O:32][C:28]=3[CH:27]=2)=[O:25])[CH:19]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[CH3:34][N:30]1[C:29]2[C:35]([CH3:37])=[CH:36][C:26]([C:24]([C:20]3[CH:19]=[C:18]([N:13]4[CH2:12][CH2:11][C:4]5([C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[NH:1][C:2](=[O:16])[NH:3]5)[CH2:15][CH2:14]4)[N:23]=[CH:22][N:21]=3)=[O:25])=[CH:27][C:28]=2[O:32][C:31]1=[O:33]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 497603501'H-Spiro[piperidine-4,4'-quinazolin]-2'(3'H)-oneHCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 252652973,4-dimethyl-6-(6-(2'-oxo-2',3'-dihydro-1'H-spiro[piperidin-4,4'-quinazolin]-1-yl)pyrimidin-4-carbonyl)benzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

87.0 mg (0.400 mmol) 1′H-spiro[piperidin-4,4′-quinazolin]-2′(3′H)-one, 122 mg (0.400 mmol) 6-(6-chloropyrimidin-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.140 mL (0.800 mmol) DIPEA were combined in 3.0 mL DMF and stirred for 48 h at RT. The reaction mixture was diluted with MeOH, the precipitate was suction filtered, washed with diethyl ether and dried.

Workup

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

Sources & evidence

ORD record
ord-60b8b28977ec4108ab54a9ac14025b9f
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

Loading…