Trifluoroacetic acid → HCID 59612565, compound

HRID 1890092Notes

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 596125087-{8-[5-Chloro-2-(2,2-difluoro-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester

Product 1

HCID 59612565HCID 59612565, compound

Procedure

{8-[5-Chloro-(2,2-difluoro-ethoxy)-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-[5-chloro-2-(2,2-difluoro-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (0.117 g, 205 mmol) and trifluoroacetic acid (0.5 mL) in a manner analogous to Example 312 to give product (0.045 g, 47%). MP=102-105° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.52 (s, 1H), 8.78 (d, 1H), 7.80 (s, 1H), 7.65 (d, 1H), 7.50 (d, 1H), 7.40 (m, 2H), 7.30 (d, 1H), 7.05 (t, 1H), 7.00 (d, 1H), 6.25 (br m, 1H), 4.35 (m, 2H), 3.10 (br m, 1H), 2.79 (br m, 8H). MS=470 (MH)+.

Sources & evidence

ORD record: ord-cc795d23238a422885146469df0ce5c7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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