2,4,6-Trimethylpyridine → 5-tert-butyl 1-ethyl 3-[(4-chloromethyl-benzoyl)amino]-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate

HRID 448135Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:12][C:13]1[C:14]2[CH:20]=[C:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[S:18][C:15]=2[NH:16][N:17]=1.N1C(C)=CC(C)=C[C:29]=1[CH3:36].[C:37](=O)([OH:39])[O-:38].[Na+]>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][C:13]2[C:14]3[CH:20]=[C:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[S:18][C:15]=3[N:16]([C:37]([O:39][CH2:29][CH3:36])=[O:38])[N:17]=2)=[O:8])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 20 °C

Procedure

4-Chloromethylbenzoyl chloride (5.42 g 28.7 mmol) was added to a suspension of tert-butyl 3-amino-1H-thieno[2,3-c]pyrazole-5-carboxylate (5.94 g, 19.1 mmol) in dry DCM (150 mL) and 2,4,6-collidine (6.94 g, 57.3 mmol) under stirring at 20° C. The resulting suspension was stirred for 3 hours at room temperature. 300 mL of aqueous sodium bicarbonate were then added to the reaction mixture and the organic layer was separated, washed with brine, dried over sodium sulphate and evaporated. The residue was triturated with hexane, filtered and dried at 40° C. under vacuum to give 8.3 g of the title compound.

Workup

stirringThe resulting suspension was stirred for 3 hours at room temperature
customthe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulphate
customevaporated
customThe residue was triturated with hexane
filtrationfiltered
customdried at 40° C. under vacuum

Sources & evidence

ORD record: ord-902743747b524328829a742c8cca5b3a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481584B2

Reaction notes

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