Dimethylformamide → HCID 56962849, compound

HRID 1037557Notes

Reaction equation

HRID 1037557 reaction equation
[CH:1]1([C:4]2[C:12]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:25]([NH:27][CH3:28])=[O:26])[N:8]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.F[C:30]1[CH:36]=CC(N)=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.CN(C=[O:56])C>CN(C1C=CN=CC=1)C>[CH:1]1([C:4]2[C:12]([N:13]([CH2:30][CH2:36][OH:56])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:25]([NH:27][CH3:28])=[O:26])[N:8]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[N:9]=3)[CH:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97314-FluoroanilineHCID 10868DicyclohexylcarbodiimideHCID 56962848HCID 56962848, compound2×

Product 1

HCID 56962849HCID 56962849, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

NB: 5-Cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide (14) was prepared following the procedure described in Method F using 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide (13) in place of 2-(4-fluorophenyl)-5-methoxy-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide (10). 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide (13) in turn was prepared according to Method A using 4-fluoroaniline in place of 4-bromoaniline in Step d. Alternatively, esterification may be carried out as for Compound (116) with a suitable carboxylic acid using a coupling agent (e.g. DCC), 4-DMAP in DMF.

Sources & evidence

ORD record
ord-7e07af4482cc404380ecbf3df604fb84
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

Loading…