8-(4-amino-3-fluorophenoxy)pyrido[2,3-b]pyrazin-3(4H)-one → 1-(2-Fluoro-4-(3-oxo-3,4-dihydropyrido[3,2-b]pyrazin-8-yloxy)phenyl)-3-(2-(pyridin-3-yloxy)-5-(trifluoromethyl)phenyl)urea

HRID 217877Notes

Reaction equation

HRID 217877 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:16]3[N:15]=[CH:14][C:13](=[O:17])[NH:12][C:11]=3[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[F:20].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:29]=2[NH:38][C:39](=O)[O:40]C2C=CC=CC=2)[CH:22]=1>>[F:20][C:3]1[CH:4]=[C:5]([O:6][C:7]2[C:16]3[N:15]=[CH:14][C:13](=[O:17])[NH:12][C:11]=3[N:10]=[CH:9][CH:8]=2)[CH:18]=[CH:19][C:2]=1[NH:1][C:39]([NH:38][C:29]1[CH:30]=[C:31]([C:34]([F:36])([F:35])[F:37])[CH:32]=[CH:33][C:28]=1[O:27][C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1)=[O:40]

Participants

3

Reactant 2

HCID 469009328-(4-amino-3-fluorophenoxy)pyrido[2,3-b]pyrazin-3(4H)-oneHCID 59588873Phenyl 2-(pyridin-3-yloxy)-5-(trifluoromethyl)phenylcarbamate

Product 1

HCID 441318821-(2-Fluoro-4-(3-oxo-3,4-dihydropyrido[3,2-b]pyrazin-8-yloxy)phenyl)-3-(2-(pyridin-3-yloxy)-5-(trifluoromethyl)phenyl)urea

Procedure

Method F2 was used with 8-(4-amino-3-fluorophenoxy)pyrido[2,3-b]pyrazin-3(4H)-one (30.6 mg, 0.112 mmol) and a 60.6 mM solution of phenyl 2-(pyridin-3-yloxy)-5-(trifluoromethyl)phenylcarbamate (1.6 ml, 0.097 mmol). After 40 h, the mixture was evaporated onto silica gel, loaded onto a Biotage 12+M column, which was eluted with 40%-100% EtOAc in DCM. Yield: 4 mg (7%).

Workup

  1. customthe mixture was evaporated onto silica gel
  2. washwas eluted with 40%-100% EtOAc in DCM

Sources & evidence

ORD record
ord-03d6fb8b116044cbb117e4f9692f95b2
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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