HCID 178501166, compound → HCID 178501077, compound

HRID 1482889Notes

Reaction equation

[F:1][CH:2]([F:39])[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]([CH:23](OS(C)(=O)=O)[C@H:24]4[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25]4)=[N:21][CH:22]=3)[CH:13]=[C:14]([CH3:16])[CH:15]=2)[N:4]=1>[Pd].C1COCC1>[F:39][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]([CH2:23][C@H:24]4[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25]4)=[N:19][CH:18]=3)[CH:13]=[C:14]([CH3:16])[CH:15]=2)[N:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of methyl trans-4-{[5-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)pyrimidin-2-yl][(methylsulfonyl)oxy]methyl}cyclohexanecarboxylate (100 mg, 0.18 mmol) and palladium on carbon (10 mg, 10 wt %) in THF (10 mL) was stirred under a hydrogen atmosphere (45 psi) at 40° C. for 48 hours. The reaction mixture was then filtrated and concentrated under reduced pressure. The residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give methyl trans-4-{[5-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)pyrimidin-2-yl]methyl}cyclohexanecarboxylate. MS ESI calc'd for C25H28F2N5O2[M+H]+ 468. found 468. 1H NMR: (400 MHz, CD3OD) δ 8.99 (s, 2H), 8.65 (d, J=4.8 Hz, 1H), 8.02 (s, 1H), 7.62 (s, 1H), 7.22 (s, 1H), 7.06 (d, J=4.8 Hz, 1H), 6.60 (t, J=54.4 Hz, 1H), 3.66 (s, 3H), 2.89 (t, J=7.2 Hz, 2H), 2.45 (s, 3H), 2.33-2.30 (m, 1H), 2.01-1.97 (m, 3H), 1.81-1.79 (m, 2H), 1.48-1.41 (m, 2H), 1.19-1.17 (m, 2H).

Workup

filtrationThe reaction mixture was then filtrated
concentrationconcentrated under reduced pressure
customThe residue was purified by prep-TLC (ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-66d79c11656341c0ab8a357b44a7739c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416111B2

Reaction notes

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