HCID 178437593, compound → HCID 178501081, compound

HRID 1482893Notes

Reaction equation

HRID 1482893 reaction equation
[F:1][CH:2]([F:35])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][C:20]([C:23]([C@H:25]4[CH2:30][CH2:29][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:26]4)=[CH2:24])=[N:21][CH:22]=3)[CH:13]=[C:14]([CH3:16])[CH:15]=2)[N:4]=1>[Pd].C1COCC1>[F:35][CH:2]([F:1])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([C:17]3[CH:22]=[N:21][C:20]([CH:23]([C@H:25]4[CH2:30][CH2:29][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:26]4)[CH3:24])=[N:19][CH:18]=3)[CH:13]=[C:14]([CH3:16])[CH:15]=2)[N:4]=1

Participants

4

Reactant 1

HCID 178437593HCID 178437593, compound

Product 1

HCID 178501081HCID 178501081, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl trans-4-{1-[5-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)pyrimidin-2-yl]ethenyl}cyclohexanecarboxylate (5 mg, 10.43 μmol) and palladium on carbon (5 mg, 10 wt %) in THF (10 mL) was stirred at 25° C. under a hydrogen atmosphere (45 psi) for 16 hours. The mixture was then filtered and the filtrate was concentrated under reduced pressure to afford methyl trans-4-{1-[5-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)pyrimidin-2-yl]ethyl}cyclohexanecarboxylate. MS ESI calc'd for C26H30F2N5O2 [M+H]+ 482. found 482.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-747bf78e8424411d81cd103fdc761792
Source dataset
uspto-grants-2016_08
Patent number
US09416111B2

Reaction notes

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