Ammonia → HCID 178512378, compound

HRID 30086Notes

Reaction equation

HRID 30086 reaction equation
[C:1]([NH:3][C:4](=[N:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]=[C:18]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[F:41])[C:19]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:20]=2[N:21]=1)OC1C=CC=CC=1)#[N:2].[NH3:42]>C(O)(C)C>[C:1]([NH:3][C:4]([NH:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]=[C:18]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[F:41])[C:19]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:20]=2[N:21]=1)=[NH:42])#[N:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59789332Phenyl N-cyano-N'-(2-{[4-(2,4-difluorophenyl)-8-(2-fluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}ethyl)imidocarbamate

Product 1

HCID 178512378HCID 178512378, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a solution of phenyl N-cyano-N′-(2-{[4-(2,4-difluorophenyl)-8-(2-fluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}-ethyl)imidocarbamate in isopropanol (2 mL) was added a 2M solution of ammonia in isopropanol (2 mL). The mixture was irradiated with microwave at about 60° C. for about 20 min. LC/MS showed a mixture containing approximately 25% product and 75% starting material. The mixture was kept in a sealed tube for 6 days. LC/MS showed 100% product. The solvent was evaporated and the residue was purified to give the title compound (20 mg, 60%). LC-MS m/z 479 (M+H)+, 2.84 min (ret time).

Workup

  1. customThe mixture was irradiated with microwave at about 60° C. for about 20 min
  2. customThe solvent was evaporated
  3. customthe residue was purified

Sources & evidence

ORD record
ord-c56afd766dff4b548377789911d76de8
Source dataset
uspto-grants-2008_09
Patent number
US07423042B2

Reaction notes

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