Ammonia → HCID 178513685, compound

HRID 2121471Notes

Reaction equation

HRID 2121471 reaction equation
O=C1CCC(=O)N1O[C:9]([C:11]1[CH:15]=[C:14]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:18]=2)[NH:13][N:12]=1)=O.[NH3:33].[OH2:34]>CN(C=O)C.O1CCOCC1>[C:9]([C:11]1[CH:15]=[C:14]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:18]=2)[NH:13][N:12]=1)(=[O:34])[NH2:33]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 178526061HCID 178526061, compound

Product 1

HCID 178513685HCID 178513685, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(2-phenyl-quinazolin-4-ylamino)-1H-pyrazole-3-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (270 mg, 0.63 mmol) in DMF (20 ml) was added a solution of ammonia in 1,4-dioxane (0.5 M, 10 ml). The resulting mixture was stirred at room temperature for 24 h. After concentration of the solvents, the residue was added to water (20 ml). The resulting precipitate was collected to afford III-100 (168 mg, 80%)as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 7.77-7.51 (m, 6H), 7.86 (br s, 2H), 8.11 (m, 1H), 8.50 (m, 2H), 8.63 (m, 1H), 10.52 (s, 1H), 11.25 (s, 1H); EI-MS 331.1 (M+H); HPLC-Method A, Rt 2.52 min.

Workup

  1. customThe resulting precipitate was collected
  2. customto afford III-100 (168 mg, 80%)as a yellow solid

Sources & evidence

ORD record
ord-c13e6d57927d41c7a6957edee7a28f56
Source dataset
uspto-grants-2004_02
Patent number
US06696452B2

Reaction notes

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