Hydrochloric Acid → HCID 89815145, compound

HRID 2172306Notes

Reaction equation

[S:1]1[C:5]([NH:6][S:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=3[C:30]3[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH:31]=3)[CH2:11]2)(=[O:9])=[O:8])=[N:4][CH:3]=[N:2]1.[ClH:43].O1CCOCC1>C(OCC)C>[ClH:43].[NH:33]1[CH2:32][CH:31]=[C:30]([C:21]2[CH:22]=[C:23]([C:26]([F:28])([F:29])[F:27])[CH:24]=[CH:25][C:20]=2[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:17]=2[CH2:18][CH2:19][N:10]([S:7]([NH:6][C:5]2[S:1][N:2]=[CH:3][N:4]=2)(=[O:8])=[O:9])[CH2:11]3)[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 80 °C

Procedure

A vial charged with tert-butyl 4-(2-(2-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.305 g, 0.491 mmol) was treated with HCl 4N in dioxane (3.07 ml, 12.26 mmol) then was heated to 80° C. for one hour. The reaction mixture was cooled to room temperature and was diluted with diethyl ether. The resulting white solid was filtered off and dried yielding 5-(2-(1,2,3,6-tetrahydropyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide hydrochloride (0.242 g, 0.434 mmol). [M+H]+=522.0. 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.81 (br. s., 2H), 8.35-8.44 (m, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.60 (d, J=1.3 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.18-7.28 (m, 2H), 7.02 (d, J=6.6 Hz, 1H), 5.72 (br. s., 1H), 4.22-4.36 (m, 2H), 3.31-3.52 (m, 4H), 3.26 (m, 2H), 2.83-3.08 (m, 2H), 1.91-2.20 (m, 2H)

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe resulting white solid was filtered off
customdried

Sources & evidence

ORD record: ord-f757a3fd92034febb1c0eb08bddaf90d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051311B2

Reaction notes

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