Aniline → N-phenyl-5-(3-fluorobenzenesulfonylamino)-1H-indazole-3-carboxamide

HRID 25382Notes

Reaction equation

HRID 25382 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[C:15]3[C:21](O)=[O:22])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CN(C)C=O>[C:58]1([NH:57][C:21]([C:15]2[C:14]3[C:18](=[CH:19][CH:20]=[C:12]([NH:11][S:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)(=[O:9])=[O:10])[CH:13]=3)[NH:17][N:16]=2)=[O:22])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22567186HCID 22567186, compound

Product 1

HCID 10454214N-phenyl-5-(3-fluorobenzenesulfonylamino)-1H-indazole-3-carboxamideYield 12.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Phenyl-5-(3-fluorobenzenesulfonylamino)-1H-indazole-3-carboxamide can be obtained as described in Example 18 from 0.45 g of 5-(3-fluorobenzenesulfonylamino)-1H-indazole-3-carboxylic acid, 11 ml of dimethylformamide, 0.56 g of 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 0.38 g of diisopropylethylamine and 0.14 g of aniline. 70 mg of N-phenyl-5-(3-fluorobenzenesulfonylamino)-1H-indazole-3-carboxamide are thus obtained in the form of a brown solid melting above 260° C. (Analysis: C20H15FN4O3S.0.73H2O % calculated C, 58.54; H, 3.68; F, 4.63; N, 13.65; O, 11.69; S, 7.81. % found C, 58.09; H, 3.18; N, 13.58; S, 7.43).

Sources & evidence

ORD record
ord-1510b2f7e2154c1f8fdc48271f6f7b52
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

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