2-tert-Butyl-1,1,3,3-tetramethylguanidine → 4-(3,3-Difluoro-cyclobutylamino)-5-methanesulfonyl-2-methyl-benzoic acid methyl ester

HRID 1815460Notes

Reaction equation

[F:1][C:2]1([F:11])[CH2:5][CH:4]([NH:6]S(C)(=O)=O)[CH2:3]1.[CH3:12][O:13][C:14](=[O:27])[C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[C:18](F)=[CH:17][C:16]=1[CH3:26].C(N=C(N(C)C)N(C)C)(C)(C)C>CN1C(=O)CCC1>[CH3:12][O:13][C:14](=[O:27])[C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:22])=[O:23])[C:18]([NH:6][CH:4]2[CH2:3][C:2]([F:1])([F:11])[CH2:5]2)=[CH:17][C:16]=1[CH3:26]

Participants

Conditions

Temperature: 150 °C

Procedure

0.70 g of N-(3,3-Difluoro-cyclobutyl)-methanesulfonamide, 0.93 g of 4-fluoro-5-methanesulfonyl-2-methyl-benzoic acid methyl ester, and 1.5 ml of N″-tert-butyl-N,N,N′,N′-tetramethyl-guanidine were dissolved using 10 ml NMP (anhydrous) and stirred for 6 h at 150° C. The reaction mixture was cooled to ambient temperature and 200 ml of EE added. This solution was washed three times using 20 ml of a saturated aqueous NaHSO4-solution each time. Thereafter, the organic layer was washed three times using 30 ml of a saturated aqueous Na2CO3-solution each time. The organic layer was dried over MgSO4 and the solvent removed in vacuo. Chromatography on silica gel using DIP yielded 220 mg of a colourless foam.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
addition200 ml of EE added
washThis solution was washed three times
washThereafter, the organic layer was washed three times
dry with materialThe organic layer was dried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-6fd7de97231d49aaadb4d63c23af7c18
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878748B2

Reaction notes

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