Trifluoroacetic acid → HCID 59612393, compound

HRID 1890075Notes

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 49839724HCID 49839724, compound

Product 1

HCID 59612393HCID 59612393, compound

Procedure

[8-(2-Fluoro-4-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine was prepared from 4-{4-[8-(2-fluoro-4-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (0.253 g, 0.488 mmol) and trifluoroacetic acid (1 mL) in a manner analogous to Example 312 to give product (0.179 g, 88%). MP=95-98° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.64 (s, 1H), 8.78 (d, 1H), 7.80 (m, 1H), 7.58 (m, 3H), 7.15 (m, 3H), 6.98 (m, 2H), 3.85 (s, 3H), 3.05 (m, 2H), 2.55 (br m, 3H), 2.25 (br m, 1H), 1.65 (m, 2H), 1.45 (m, 2H). MS=418 (MH)+.

Sources & evidence

ORD record: ord-d6d4dd6df491455b94bfaf24ef61a7ce
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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