Pyridine → HCID 57908849, compound

HRID 222388Notes

Reaction equation

HRID 222388 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([NH:27][C:28]([NH:30][CH2:31][C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[F:39])=[O:29])=[CH:24][CH:25]=2)[C:20]([NH2:40])=[N:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:40][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]([NH:27][C:28]([NH:30][CH2:31][C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[F:39])=[O:29])[CH:22]=2)[N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[N:19]=1)=[O:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 69252Benzoyl chloride, 3-chloro-HCID 57908839HCID 57908839, compound

Product 1

HCID 57908849HCID 57908849, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

7.1 93 mg of 3-chlorobenzoyl chloride are added to a mixture of 200 mg of tert-butyl-3-amino-5-[3-(2,5-difluorobenzyl)ureido]indazole-1-carboxylate (0.48 mmol, preparation analogous to Example 1.1), 2.0 ml of pyridine, 8 mg of 4-(dimethylamino)pyridine and 100 μl of dioxane, and the mixture is stirred at 90° C. for 24 hours. After cooling, the batch is evaporated, and the residue is purified by column chromatography on silica gel (eluent:heptane/EA 3:2), giving 90 mg of tert-butyl 3-(3-chlorobenzoylamino)-5-[3-(2,5-difluorobenzyl)ureido]indazole-1-carboxylate (34%), MS-FAB (M+H+)=556.

Workup

  1. temperatureAfter cooling
  2. customthe batch is evaporated
  3. customthe residue is purified by column chromatography on silica gel (eluent:heptane/EA 3:2)

Sources & evidence

ORD record
ord-2daf8aeaa1e94761927d7701e1e53ae7
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

Loading…