Trifluoroacetic acid → [8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine

HRID 472595Notes

Reaction equation

C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19]3[N:39]=[C:22]4[C:23]([C:27]5[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=5[O:37][CH3:38])=[CH:24][CH:25]=[CH:26][N:21]4[N:20]=3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:38][O:37][C:28]1[CH:29]=[CH:30][C:31]([C:33]([F:36])([F:34])[F:35])=[CH:32][C:27]=1[C:23]1[C:22]2[N:21]([N:20]=[C:19]([NH:18][C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[CH2:9][NH:8][CH2:17][CH2:16]4)[N:39]=2)[CH:26]=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 596126096-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 49838140[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine

Procedure

[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine was prepared from 6-[8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester and trifluoroacetic acid (1 mL) in a manner analogous to Example 312 to give product (0.255 g). MP=99-103° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.47 (s, 1H), 8.79 (d, 1H), 7.95 (s, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.38 (m, 3H), 7.05 (t, 1H), 6.85 (d, 1H), 3.85 (s, 3H), 3.75 (s, 2H), 2.92 (m, 2H), 2.63 (br m, 3H): MS=440 (MH)+.

Sources & evidence

ORD record: ord-79ca84f8ca75426e988ad3178d58a513
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

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