Ammonia → HCID 178513685, compound

HRID 472180Notes

Reaction equation

HRID 472180 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-fed942ce1e39490f91b36299f7a30929
Source dataset
uspto-grants-2014_01
Patent number
US08633210B2

Reaction notes

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