Ethanolamine → HCID 118208967, compound

HRID 595280Notes

Reaction equation

[OH:1][C@@H:2]([CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:16]=[C:15]([CH3:30])[CH:14]=2)[CH:10]=[N:9]1)[C:3](OC)=[O:4].[CH2:31]([CH2:33][NH2:34])[OH:32]>CO>[OH:1][C@@H:2]([CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[CH:22][N:21]=3)[CH:16]=[C:15]([CH3:30])[CH:14]=2)[CH:10]=[N:9]1)[C:3]([NH:34][CH2:33][CH2:31][OH:32])=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Methyl (2S)-2-hydroxy-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanoate (40 mg, 0.10 mmol) in methanol (1 mL) was treated with ethanolamine (0.03 mL, 0.48 mmol). The mixture was stirred overnight at 70° C. Upon cooling to room temperature, the mixture was filtered and purified by reverse phase HPLC (0 to 95% ACN/water with 0.1% TFA modifier) to afford (2S)-2-hydroxy-N-(2-hydroxyethyl)-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanamide. MS ESI calcd. for C20H21F3N6O3 [M+H]+ 451. found 451. 1H NMR (500 MHz, DMSO-d6) δ 10.11 (s, 1H), 8.80 (d, J=4.9 Hz, 1H), 7.94 (s, 1H), 7.84 (t, J=5.6 Hz, 1H), 7.80 (s, 1H), 7.75 (s, 1H), 7.33 (s, 1H), 7.23 (d, J=6.3 Hz, 1H), 7.05 (s, 1H), 4.39 (dd, J=2.9 Hz, 13.7 Hz, 1H), 4.26 (d, J=7.7 Hz, 1H), 4.17-4.12 (m, 1H), 3.38 (t, J=5.9 Hz, 2H), 3.16 (q, J=6.1 Hz, 2H), 2.28 (s, 3H).

Workup

temperatureUpon cooling to room temperature
filtrationthe mixture was filtered
custompurified by reverse phase HPLC (0 to 95% ACN/water with 0.1% TFA modifier)

Sources & evidence

ORD record: ord-7eb9db759a7e4a449f8409a2f1fb81e5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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