Trifluoroacetic acid → HCID 59612361, compound

HRID 472610Notes

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:39]=[C:24]4[C:25]([C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=5[O:37][CH3:38])=[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>>[CH3:38][O:37][C:30]1[C:31]([O:35][CH3:36])=[CH:32][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[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[CH:15][CH:16]=3)[N:39]=2)[CH:28]=[CH:27][CH:26]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 596125464-{4-[8-(2,3-Dimethoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59612361HCID 59612361, compound

Procedure

[8-(2,3-Dimethoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine was prepared from 4-{4-[8-(2,3-dimethoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (0.264 g, 0.499 mmol) and trifluoroacetic acid (1 mL) in a manner analogous to Example 312 to give product (0.203 g, 95%). MP=94-97° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.52 (s, 1H), 8.78 (d, 1H), 7.52 (m, 3H), 7.15 (m, 6H), 3.87 (s, 3H), 3.59 (s, 3H), 3.05 (m, 2H), 2.55 (m, 4H), 1.62 (m, 2H), 1.45 (m, 2H). MS=430 (MH)+.

Sources & evidence

ORD record: ord-94206be03bab45e7a25973a16a465c17
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

Loading…