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

HRID 1582386Notes

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.S(O)(O)(=O)=O.CS[C:24](=[NH:26])[NH2:25].[OH-].[Na+]>O>[C:24]([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:25])[NH2:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred suspension of N-(1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide hydrochloride prepared as described in Example 19(b) of WO 98/30560 (100 g, 0.38 mol) and 2-methyl-2-thiopseudourea sulfate (159 g, 0.57 mol) in water (1.5 liter) was added 2N aqueous sodium hydroxide (764 ml, 1.53 mol). The resulting solution was warmed to 80° C. and stirred at this temperature for 6 hours and then left to cool to room temperature overnight. Further 2-methyl-2-thiopseudourea sulfate (27 g, 0.10 mol) and 2N aq. sodium hydroxide (48 ml, 0.10 mol) were charged and the mixture heated at 80° C. for 1 hour. After this time the resulting suspension was cooled to room temperature, filtered, washed with water (1 liter) to give a white solid that was dried in vacuo overnight at 50° C. to give 91.0 g of the title product (89%).

Workup

customprepared
waitleft
temperatureto cool to room temperature overnight
temperaturethe mixture heated at 80° C. for 1 hour
temperatureAfter this time the resulting suspension was cooled to room temperature
filtrationfiltered
washwashed with water (1 liter)
customto give a white solid
customthat was dried in vacuo overnight at 50° C.

Sources & evidence

ORD record: ord-3a9383cd42db4fbd9500fa28d9ebf5cb
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734303B2

Reaction notes

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