Diphenyl N-Cyanocarbonimidate → Phenyl N-cyano-N'-(2-{[8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}ethyl)imidocarbamate

HRID 30083

Reaction equation

HRID 30083 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[C:8]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([C:16]3[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=3[F:23])[C:9]=2[N:10]=1.[CH:32]1[CH:37]=[CH:36][C:35]([O:38][C:39](OC2C=CC=CC=2)=[N:40][C:41]#[N:42])=[CH:34][CH:33]=1>C(O)(C)C>[C:41]([NH:40][C:39](=[N:1][CH2:2][CH2:3][NH:4][C:5]1[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[C:8]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([C:16]3[C:17]([F:23])=[CH:18][CH:19]=[CH:20][C:21]=3[F:22])[C:9]=2[N:10]=1)[O:38][C:35]1[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=1)#[N:42]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 596395772-[(2-Aminoethyl)amino]-8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 59789334Phenyl N-cyano-N'-(2-{[8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}ethyl)imidocarbamate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound from Example 8 [8-(2,6-Difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-[(2-aminoethyl)amino]-8H-pyrido[2,3-d]pyrimidin-7-one](0.382 g, 0.0009 mol) was treated with stirring with diphenylcyanocarbonimidate (0.214 g, 0.0009 mol) in isopropanol (5 mL). Stirred at 23° for 0.5 hours. LC/MS showed a new major peak corresponding to the desired product and no starting material in the solution. LC MS (m/e)=570(MH+). Rt=2.24 min.

Sources & evidence

ORD record
ord-a6eb4884d534449dbc2caff6019af854
Source dataset
uspto-grants-2008_09
Patent number
US07423042B2

Linked notes

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