Hydrochloric Acid → N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide

HRID 1795390Notes

Reaction equation

S(O)(O)(=O)=O.[CH2:6]1[C:15]2[C:10](=[C:11]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.[CH2:21]1C2C(=C(NS(C)(=O)=O)C=CC=2)CC[NH:22]1.S(=O)(=O)(O)O.Cl.C(N(CC)C(C)C)(C)C.N#CBr>C(#N)C.O>[C:21]([N:7]1[CH2:8][CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:6]1)#[N:22]

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred slurry of N-(1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide hemisulfate (prepared analogously to the compound of Example 19(b) in WO 98/30560, but using sulphuric acid in the final step in place of hydrochloric acid; 240 g, 0.88 mol) in acetonitrile (2400 ml) at 0° C. was added N,N-diisopropylethylamine (326 ml, 1.88 mmol). Cyanogen bromide (99.2 g, 0.94 mol) was added over a period of 20 minutes keeping the temperature below 10° C. The resulting slurry was allowed to warm to 20° C. and stirred at this temperature for 18 hrs. After this time, water (2400 ml) was added and the resulting mixture extracted with CH2Cl2 (2×2500 ml). The combined organic phases were washed with water (2000 ml) and evaporated to dryness. The resulting solid was reslurried in CH2Cl2 (360 ml) and the solid collected by filtration to yield 158 g (72%) of the title compound.

Workup

customthe temperature below 10° C
extractionthe resulting mixture extracted with CH2Cl2 (2×2500 ml)
washThe combined organic phases were washed with water (2000 ml)
customevaporated to dryness
filtrationthe solid collected by filtration

Sources & evidence

ORD record: ord-20be178531594e329c72d756d4f45ba3
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026479B2

Reaction notes

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