Ethanolamine → HCID 118092668, compound

HRID 2207394Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].F[C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]([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:15]=[C:16]([CH3:18])[CH:17]=2)[CH:9]=[N:10][CH:11]=1.[H-].[Na+]>C1COCC1>[CH3:18][C:16]1[CH:17]=[C:12]([C:8]2[CH:7]=[C:6]([NH:4][CH2:3][CH2:1][OH:2])[CH:11]=[N:10][CH:9]=2)[CH:13]=[C:14]([NH:19][C:20]2[N:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][N:21]=2)[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethanolamine (26.3 mg, 0.431 mmol) was added to a mixture of N-[3-(5-fluoropyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine (50.0 mg, 0.144 mmol) and sodium hydride (17.2 mg, 0.431 mmol) in THF (0.718 mL, 0.2 M). The reaction mixture was heated overnight at 80° C. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with chloroform. The organic layer was concentrated in vacuo and purified by reverse phase liquid chromatography (10:90 to 60:40, acetonitrile:water) afforded 2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]amino}ethanol as the formic acid salt. MS APCI calc'd for C19H19F3N5O [M+H]+ 390. found 390. 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H), 8.83 (d, J=4.9 Hz, 1H), 8.48 (s, 1H), 8.34 (d, J=2.6 Hz, 1H), 7.99 (d, J=11.4 Hz, 3H), 7.59 (d, J=26.7 Hz, 2H), 7.34-7.12 (m, 2H), 4.33 (t, J=4.9 Hz, 2H), 3.77 (br s, 3H), 3.27 (t, J=5.3 Hz, 2H).

Workup

customThe reaction mixture was quenched with saturated aqueous NH4Cl
extractionextracted with chloroform
concentrationThe organic layer was concentrated in vacuo
custompurified by reverse phase liquid chromatography (10:90 to 60:40, acetonitrile:water)

Sources & evidence

ORD record: ord-7159195d85fd4abe94e9cc1bda259a1d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376418B2

Reaction notes

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