Trifluoroacetic acid → HCID 59612463, compound

HRID 1890057Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:40]=[C:24]4[C:25]([C:29]5[CH:34]=[CH:33][C:32]([CH:35]([F:37])[F:36])=[CH:31][C:30]=5[O:38][CH3:39])=[CH:26][CH:27]=[CH:28][N:23]4[N:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[F:37][CH:35]([F:36])[C:32]1[CH:33]=[CH:34][C:29]([C:25]2[C:24]3[N:23]([N:22]=[C:21]([NH:20][C:17]4[CH:16]=[CH:15][C:14]([CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:19][CH:18]=4)[N:40]=3)[CH:28]=[CH:27][CH:26]=2)=[C:30]([O:38][CH3:39])[CH:31]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59612611HCID 59612611, compound

Product 1

HCID 59612463HCID 59612463, compound

Procedure

[8-(4-Difluoromethyl-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine was prepared from 4-{4-[8-(4-difluoromethyl-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (0.191 g, 0.348 mmol) and trifluoroacetic acid (0.500 mL) in a manner analogous to Example 312 to give product (0.170 g, 99%). MP=208-212° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.57 (s, 1H), 8.78 (d, 1H), 7.70 (d, 1H), 7.55 (m, 3H), 7.32 (s, 1H), 7.25 (m, 1H), 7.15 (m, 3H), 7.10 (br m, 1H), 3.78 (s, 3H), 3.28 (br m, 3H), 2.92 (m, 2H), 2.65 (m, 1H), 1.83 (m, 2H), 1.65 (m, 2H): MS=450 (MH)+.

Sources & evidence

ORD record: ord-77ac833921f342f5b4143b9b2d6793c1
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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