Hydrochloric Acid → 5-(2-(2,5-dihydro-1H-pyrrol-3-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide hydrochloride

HRID 2172312Notes

Reaction equation

HRID 2172312 reaction equation
CC1(C)C(C)(C)OB(C2CN(C(OC(C)(C)C)=O)CC=2)O1.[S:22]1[C:26]([NH:27][S:28]([N:31]2[CH2:40][CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][C:37]=3[C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][C:42]=3[C:51]3[CH2:52][N:53](C(OC(C)(C)C)=O)[CH2:54][CH:55]=3)[CH2:32]2)(=[O:30])=[O:29])=[N:25][CH:24]=[N:23]1.[ClH:63]>O1CCOCC1>[ClH:63].[NH:53]1[CH2:54][CH:55]=[C:51]([C:42]2[CH:43]=[C:44]([C:47]([F:50])([F:48])[F:49])[CH:45]=[CH:46][C:41]=2[C:37]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:38]=2[CH2:39][CH2:40][N:31]([S:28]([NH:27][C:26]2[S:22][N:23]=[CH:24][N:25]=2)(=[O:30])=[O:29])[CH2:32]3)[CH2:52]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15836637tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylateHCID 89815476tert-butyl 3-(2-(2-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 898152785-(2-(2,5-dihydro-1H-pyrrol-3-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, except that tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate was used in place of (2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid and the resulting product, (tert-butyl 3-(2-(2-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate), was converted to the final product by treatment with 50 equivalents of HCl in dioxane. The reaction mixture was concentrated under a vacuum to provide 5-(2-(2,5-dihydro-1H-pyrrol-3-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide hydrochloride. [M+H]+=508.8 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.36 (br. s., 2H), 8.38 (s, 1H), 7.73-7.83 (m, 2H), 7.43 (d, J=7.8 Hz, 1H), 7.23-7.33 (m, 2H), 6.97-7.16 (m, 2H), 5.77 (br. s., 1H), 4.20-4.38 (m, 2H), 3.92 (br. s., 2H), 3.74 (br. s., 2H), 3.64 (t, J=6.7 Hz, 1H), 3.41 (t, J=6.3 Hz, 1H), 3.26-3.36 (m, 1H), 3.12-3.24 (m, 1H)

Workup

  1. concentrationThe reaction mixture was concentrated under a vacuum

Sources & evidence

ORD record
ord-aba34a2d3a3b43bca412775f2a9110dc
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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