Sodium Hydroxide → N-(2-amidino-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide

HRID 1582387Notes

Reaction equation

HRID 1582387 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[C:7]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.Cl.[N:18]1([C:23](N)=[NH:24])C=CC=N1.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN(C=O)C>[C:23]([N:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:2]1)(=[NH:18])[NH2:24]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 22218092N-(1,2,3,4-tetrahydroisoquinolin-5-yl)methanesulfonamide hydrochloride

Product 1

HCID 11369197N-(2-amidino-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of N-(1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide hydrochloride obtainable by the method of Example 19(b) of WO 98/30560 (15 g, 69 mmol), 1H-pyrazole-1-carboxamidine hydrochloride (10.0 g, 0.57 mol) and diisopropylethylamine (16.2 g, 125 mmol) in DMF (119 ml) was stirred overnight at room temperature. After this time 2N aqueous sodium hydroxide-was added to adjust to pH 12. The resulting white suspension was stirred for three hours, filtered and the solid dried in vacuo overnight at 45° C. to give 14.5 g of the title product (95%).

Workup

  1. stirringThe resulting white suspension was stirred for three hours
  2. filtrationfiltered
  3. customthe solid dried in vacuo overnight at 45° C.

Sources & evidence

ORD record
ord-a034bb99020147f1abcf70de7e56505d
Source dataset
uspto-grants-2004_05
Patent number
US06734303B2

Reaction notes

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