Trifluoroacetic acid → HCID 49839841, compound

HRID 1890094Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([NH:19][C:20]3[N:43]=[C:23]4[C:24]([C:28]5[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:29]=5[O:38][CH2:39][CH:40]([CH3:42])[CH3:41])=[CH:25][CH:26]=[CH:27][N:22]4[N:21]=3)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH2:39]([O:38][C:29]1[CH:30]=[CH:31][C:32]([C:34]([F:36])([F:35])[F:37])=[CH:33][C:28]=1[C:24]1[C:23]2[N:22]([N:21]=[C:20]([NH:19][C:17]3[CH:16]=[CH:15][C:12]4[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=4[CH:18]=3)[N:43]=2)[CH:27]=[CH:26][CH:25]=1)[CH:40]([CH3:42])[CH3:41]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68779011HCID 68779011, compound

Product 1

HCID 49839841HCID 49839841, compound

Procedure

[8-(2-Isobutoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine was prepared from 7-[8-(2-isobutoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (0.263 g, 0.442 mmol) and trifluoroacetic acid (0.5 mL) in a manner analogous to Example 312 to give product (0.190 g, 87%). MP=102-103° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.47 (s, 1H), 8.78 (d, 1H), 7.98 (s, 1H), 7.75 (d, 1H), 7.62 (d, 1H), 7.35 (m, 3H), 7.05 (t, 1H), 6.98 (d, 1H), 3.87 (d, 2H), 2.62-2.75 (br m, 9H), 1.85 (m, 1H), 0.81 (d, 6H). MS=496 (MH)+.

Sources & evidence

ORD record: ord-2d50d91dbc434262b20a35e5df31a642
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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