Trifluoroacetic acid → HCID 59612407, compound

HRID 1890063Notes

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67481510HCID 67481510, compound

Product 1

HCID 59612407HCID 59612407, compound

Procedure

[8-(3-Methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine was prepared from 4-{4-[8-(3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (0.405 g, 0.812 mmol) and trifluoroacetic acid (2 mL) in a manner analogous to Example 312 to give product (0.150 g, 46%). MP=88-90° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.60 (s, 1H), 8.78 (d, 1H), 7.85 (m, 2H), 7.65 (m, 3H), 7.40 (m, 1H), 7.15 (m, 3H), 7.05 (m, 1H), 3.86 (s, 3H), 3.00 (m, 2H), 2.55 (m, 3H), 2.35 (br m, 1H), 1.65 (m, 2H), 1.45 (m, 2H). MS=400 (MH)+.

Sources & evidence

ORD record: ord-77a17d73fd4140d0b948f3be603b36b6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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