Réaction #165832

ord-5bdc5e4fde9a42e08ec7ec4e1f8bcfc9

Équation de réaction

CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CCN(CC)CC
Et3N
CC(C)S(=O)(=O)c1ccc(-c2cnc(N)c(C(=O)O)n2)cc1
3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carboxylic acid
NNC(N)=S
aminothiourea
CC(C)S(=O)(=O)c1ccc(-c2cnc(N)c(C(=O)NNC(N)=S)n2)cc1
resultant precipitate
CC(C)S(=O)(=O)c1ccc(-c2cnc(N)c(C(=O)NNC(N)=S)n2)cc1
2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinecarbothioamide

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

TBTU (749.4 mg, 2.334 mmol) and Et3N (157.5 mg, 216.9 μL, 1.556 mmol) were added to a suspension of 3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carboxylic acid (500 mg, 1.556 mmol) and aminothiourea (141.8 mg, 1.556 mmol) in DMF (10 mL). The reaction was allowed to stir at ambient temperature for 1 h. The reaction mixture was added to rapidly stirring water and the resultant precipitate isolated by filtration to give the product as a khaki solid (587 mg, 96%) 1H NMR (400 MHz, DMSO) d 1.18 (d, 6H), 3.40-3.56 (m, 1H), 7.64 (s, 2H), 7.79 (s, 2H), 7.88 (d, 2H), 8.56 (d, 1H), 9.03 (s, 1H), 9.41 (s, 1H) and 10.75 (s, 1H) ppm; MS (ES+) 395.2

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08841308B2uspto-grants-2014_09