Hydrochloric Acid → 3-(3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)propane-1-sulfonic acid

HRID 1470084Notes

Reaction equation

HRID 1470084 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][S:5]([OH:8])(=[O:7])=[O:6].C(=O)(O)[O-].[Na+].[Cl:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[CH2:21][N:20]([CH3:26])[CH2:19][CH:18]2[C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1.Cl>O1CCCC1.O>[Cl:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[CH2:21][N:20]([CH3:26])[CH2:19][CH:18]2[C:27]1[CH:28]=[C:29]([S:33]([NH:1][CH2:2][CH2:3][CH2:4][S:5]([OH:8])(=[O:7])=[O:6])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1646TramiprosateHCID 516892Sodium BicarbonateHCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 866723313-(3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)propane-1-sulfonic acidYield 4.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 3-aminopropane-1-sulfonic acid (180 mg, 1.29 mmol, 1.00 equiv) in tetrahydrofuran/water (10/10 mL) with sodium bicarbonate (430 mg, 5.12 mmol). This was followed by the addition of 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (500 mg, 1.29 mmol, 0.99 equiv) in several batches. The resulting solution was stirred for 4 h at room temperature. The reaction progress was monitored by LCMS. The pH value of the solution was adjusted to 6 with 1M hydrogen chloride. The resulting mixture was concentrated under vacuum. The crude product (500 mg) was purified by preparative HPLC to give 26.7 mg of the title compound (4%) as a TFA salt. 1H-NMR (300 MHz, DMSO, ppm): 10.28 (s, 1H), 7.53˜7.79 (m, 6H), 6.83 (s, 1H), 4.74 (s, 2H), 4.51 (s, 1H), 3.90 (s, 1H), 3.06 (s, 3H), 2.86˜2.93 (m, 2H), 2.33˜2.44 (m, 2H), 1.58˜1.63 (m, 2H). MS (ES, m/z): 493 [M+H]+.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe crude product (500 mg) was purified by preparative HPLC

Sources & evidence

ORD record
ord-8ae6e95657da4c28ba79ce23c14387be
Source dataset
uspto-grants-2015_04
Patent number
US09006281B2

Reaction notes

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