Trifluoroacetic acid → HCID 49839725, compound

HRID 472613Notes

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 596124024-{4-[8-(4-Cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 49839725HCID 49839725, compound

Procedure

4-[2-(4-Piperidin-4-yl-phenylamino)-[1,2,4]triazolo[1,5-a]pyridine-8-yl]benzonitrile was prepared from 4-{4-[8-(4-cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (0.181 g, 0.366 mmol) and trifluoroacetic acid (0.500 mL) in a manner analogous to Example 312 to give product (0.130 g, 90%). MP=228-232° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.70 (s, 1H), 8.85 (d, 1H), 8.40 (d, 2H), 8.00 (m, 3H), 7.62 (d, 2H), 7.15 (m, 3H), 3.05 (m, 2H), 2.60 (br m, 4H), 1.65 (m, 2H), 1.45 (m, 2H). MS=395 (MH)+.

Sources & evidence

ORD record: ord-156338000a3841a6ac8f28f85d21e15d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

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