Chlorosuccinimide → HCID 118290414, compound

HRID 628481Notes

Reaction equation

HRID 628481 reaction equation
[CH:1]1([C:4]2[C:5]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:29]=[C:28]([CH3:30])[N:27]([CH3:31])[N:26]=4)=[CH:21][C:20]=3[CH3:32])=[C:6]([N:10]3[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]3)[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.[Cl:33]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[C:5]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[C:29]([Cl:33])=[C:28]([CH3:30])[N:27]([CH3:31])[N:26]=4)=[CH:21][C:20]=3[CH3:32])=[C:6]([N:10]3[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]3)[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 118290403HCID 118290403, compound2×

Product 1

HCID 118290414HCID 118290414, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-{3-cyclopropyl-2-(2-methyl-4-(1,5-dimethyl-1H-pyrazol-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (described in Preparation example 15) (Present compound 15) 0.37 g, N-chlorosuccinimide 0.12 g and chloroform 5 ml was stirred at room temperature for twelve hours. The resulting mixture was extracted with chloroform and was washed with saturated saline. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-{3-cyclopropyl-2-(2-methyl-4-(4-chloro-1,5-dimethyl-1H-pyrazol-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Present compound 36”) 0.13 g.

Workup

  1. extractionThe resulting mixture was extracted with chloroform
  2. washwas washed with saturated saline
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-0322b079522c48f6b62fd427451f77b5
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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