Trifluoroacetic acid → HCID 59612573, compound

HRID 1890078Notes

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][CH:32]=[C:31]([N:35]([CH3:37])[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][N:35]([CH3:37])[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:38]=3)[CH:28]=[CH:27][CH:26]=2)[CH:34]=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 49839726HCID 49839726, compound

Product 1

HCID 59612573HCID 59612573, compound

Procedure

[8-(3-Dimethylamino-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine was prepared from 4-{4-[8-(3-dimethylamino-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (0.288 g, 0.563 mmol) and trifluoroacetic acid (1 mL) in a manner analogous to Example 312 to give product (0.218 g, 94%). MP=104-108° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.56 (s, 1H), 8.74 (d, 1H), 7.82 (d, 1H), 7.62 (d, 2H), 7.50 (s, 1H), 7.32 (m, 2H), 7.15 (m, 3H), 6.80 (d, 1H), 3.65 (br m, 1H), 3.15 (m, 2H), 3.00 (s, 6H), 2.60 (br m, 3H), 1.65 (m, 2H), 1.45 (m, 2H). MS=413 (MH)+.

Sources & evidence

ORD record: ord-30022f0745d0439486153db05e22f320
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

Loading…