Sodium hydride → HCID 86743842, compound
Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:25]([O:27][C:28]([N:30]=[C:31]=[S:32])=[O:29])[CH3:26]>O1CCCC1>[NH2:20][C:18]([C:17]1[CH:16]=[N:15][N:14]2[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:21])([F:1])[F:22])[CH:4]=3)=[CH:10][CH2:11][N:12]([C:31]([NH:30][C:28](=[O:29])[O:27][CH2:25][CH3:26])=[S:32])[C:13]=12)=[O:19]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of 3.0 g of 4,5-dihydro-7[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (prepared as described in Example 4) in 90 ml of dry tetrahydrofuran, cooled to -78° C. was added 584 mg of sodium hydride (60% dispersion in mineral oil) in one portion. The reaction mixture was stirred at -78° C. for one hour followed by the addition of 2.55 g of ethoxycarbonyl isothiocyanate. The mixture was stirred at -78° C. for 2 hours then was allowed to warm slowly to room temperature. The reaction mixture was stirred at room temperature for 48 hours, then was quenched with water and extracted with ether. The aqueous layer was separated, neutralized with 5% hydrochloric acid and extracted with chloroform. The chloroform extracts were evaporated in vacuo to give the product of the example as a yellow solid.
Workup
- stirringThe mixture was stirred at -78° C. for 2 hours
- temperatureto warm slowly to room temperature
- stirringThe reaction mixture was stirred at room temperature for 48 hours
- customwas quenched with water
- extractionextracted with ether
- customThe aqueous layer was separated
- extractionextracted with chloroform
- customThe chloroform extracts were evaporated in vacuo
- customto give the product of the example as a yellow solid
Sources & evidence
- ORD record
- ord-8c9c3a984e6645f983a6218555b34dc1
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04916137
Reaction notes
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