Trifluoroacetic acid → 3-(6-Fluoro-1,3-benzoxazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyrazin-2-amine

HRID 908378Notes

Reaction equation

HRID 908378 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:18]2[CH:19]=[N:20][N:21]([CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH:22]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=2[N:12]=1.C(O)(C(F)(F)F)=O>>[F:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:18]4[CH:19]=[N:20][N:21]([CH:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]5)[CH:22]=4)[N:6]=3)[O:9][C:10]=2[CH:16]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67387653Tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 576870193-(6-Fluoro-1,3-benzoxazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyrazin-2-amineYield 58.1%

Procedure

Using analogous procedures to those described in Example 17, tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate (100 mg) was reacted with TFA to give 3-(6-fluoro-1,3-benzoxazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyrazin-2-amine (46 mg). NMR Spectrum: (400 MHz, MeOD) 8.60 (s, 1H), 8.35 (s, 1H), 8.20 (s, 1H), 7.90 (dd, 1H), 7.60 (dd, 1H), 7.30 (dd, 1H), 4.20 (m, 1H), 3.70 (m, 1H), 3.30 (m, 2H), 2.50 (m, 4H); Mass spectrum: M+H+ 380

Sources & evidence

ORD record
ord-1849d5d6f7aa4900837d048f0a10d8a3
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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