Sulfuric Acid → HCID 118208734, compound

HRID 595278Notes

Reaction equation

S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:8]=[C:9]([C:24]2[CH:25]=[N:26][N:27]([CH2:29][C@@H:30]([C:32]([OH:34])=[O:33])[NH2:31])[CH:28]=2)[CH:10]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:12]=1.[C:35](=O)(O)[O-].[Na+]>CO>[CH3:6][C:7]1[CH:8]=[C:9]([C:24]2[CH:25]=[N:26][N:27]([CH2:29][C@@H:30]([C:32]([O:34][CH3:35])=[O:33])[NH2:31])[CH:28]=2)[CH:10]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:17]=[CH:16][N:15]=2)[CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Concentrated sulfuric acid (16 uL, 0.3 mmol) was added to a stirred solution of 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]-L-alanine (100 mg, 0.3 mmol) in MeOH (1 mL). The reaction mixture was heated to 70° C. overnight, cooled to room temperature, and treated with aqueous sodium bicarbonate solution. The mixture was extracted with EtOAc, washed with sodium hydroxide solution (1N, 2×) and brine, dried over sodium sulfate, concentrated under reduced pressure to afford methyl 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]-L-alaninate. MS ESI calcd. for C19H26F3N6O2 [M+H]+ 421. found 421. 1H NMR (500 MHz, DMSO-d6) δ 10.13 (s, 1H), 8.82 (d, J=4.9 Hz, 1H), 8.00 (s, 1H), 7.81 (s, 1H), 7.76 (s, 1H), 7.34 (s, 1H), 7.26 (d, J=4.6 Hz, 1H), 7.06 (s, 1H), 4.25-4.34 (m, 2H), 3.78-3.80 (m, 1H), 3.62 (s, 3H), 2.30 (s, 3H).

Workup

temperaturecooled to room temperature
extractionThe mixture was extracted with EtOAc
washwashed with sodium hydroxide solution (1N, 2×) and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b6112c64d5c84e8c932771e9d766a05f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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