Trifluoroacetic acid → HCID 59612399, compound

HRID 1890082Notes

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:39]=[C:23]4[C:24]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[O:34][CH2:35][CH:36]([F:38])[F:37])=[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>>[F:38][CH:36]([F:37])[CH2:35][O:34][C:29]1[CH:30]=[CH:31][CH:32]=[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:39]=2)[CH:27]=[CH:26][CH:25]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59612334HCID 59612334, compound

Product 1

HCID 59612399HCID 59612399, compound

Procedure

{8-[2-(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-[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 (0.388 g, 0.725 mmol) and trifluoroacetic acid (1 mL) in a manner analogous to Example 312 to give product (0.264 g, 84%). MP=87-90° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.46 (s, 1H), 8.75 (d, 1H), 7.65 (m, 2H), 7.42 (m, 2H), 7.35 (s, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 6.98 (m, 1H), 6.22 (br m, 1H), 4.32 (m, 2H), 2.70 (br m, 9H). MS=436 (MH)+.

Sources & evidence

ORD record: ord-45b3898c13f3439c8303b59cb6fdc03b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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