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

HRID 2096366Notes

Reaction equation

HRID 2096366 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:10]2[CH:19]=[C:18]([CH3:20])[C:13]3[NH:14][C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[O:9])[CH:3]=1.[NH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[NH:23][C:22]1=[O:36].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:20][C:18]1[C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=[C:10]([C:8]([C:4]2[CH:3]=[C:2]([N:33]3[CH2:32][CH2:31][C:24]4([C:25]5[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=5)[NH:21][C:22](=[O:36])[NH:23]4)[CH2:35][CH2:34]3)[N:7]=[CH:6][N:5]=2)=[O:9])[CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 497603501'H-Spiro[piperidine-4,4'-quinazolin]-2'(3'H)-oneHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 252296614-methyl-6-(6-(2'-oxo-2',3'-dihydro-1'H-spiro[piperidin-4,4'-quinazolin]-1-yl)pyrimidine-4-carbonyl)benzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

144 mg (0.500 mmol) 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one, 108 mg (0.500 mmol) 1′H-spiro[piperidin-4,4′-quinazolin]-2′(3′H)-one and 0.174 mL (1.00 mmol) DIPEA were combined in 5.0 mL DMF and stirred overnight at RT. The reaction mixture was purified by preparative HPLC, the fractions containing the product were combined and the organic solvent was eliminated i.vac. The aqueous phase was neutralised by the addition of 4N aqueous NaOH solution. The product precipitated as a solid was filtered off, washed with water and dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC
  2. additionthe fractions containing the product
  3. additionThe aqueous phase was neutralised by the addition of 4N aqueous NaOH solution
  4. customThe product precipitated as a solid
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-abfc4ac1092f4c77925486600cb84c06
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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