Sodium hydride → HCID 178424291, compound

HRID 863046Notes

Reaction equation

HRID 863046 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[N:16][NH:17][C:11]=3[C:10]3[S:18][CH:19]=[CH:20][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:25]1([CH3:34])[C:26]([C:31](Cl)=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=1>O1CCOCC1>[N:17]1[NH:16][CH:15]=[C:12]2[CH2:13][CH2:14][N:8]([C:6]([C:5]3[CH:21]=[CH:22][C:2]([NH:1][C:31](=[O:32])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH3:34])=[CH:3][CH:4]=3)=[O:7])[C:9]3[CH:20]=[CH:19][S:18][C:10]=3[C:11]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 702762-Methylbenzoyl chlorideHCID 19699095HCID 19699095, compound

Product 1

HCID 178424291HCID 178424291, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 400 mg of 6-(4-aminobenzoyl)-1,4,5,6-tetrahydropyrazolo[3,4-d]thieno[3,2-b]azepine in 12.0 ml of dioxane under argon is added 65 mg of sodium hydride (60% in mineral oil). After stirring for 15 minutes, 176 μl of o-toluoyl chloride is added. The reaction mixture is stirred at room temperature for 18 hours under argon. The reaction mixture is evaporated in vacuo to a residue which is dissolved in 40 ml of methylene chloride and washed with 20 ml each of water and brine. The organic layer is dried (Na2 SO4) and filtered. The filtrate is concentrated in vacuo to give a residue which is purified by chromatography on silica gel plates by elution with 1:1 ethyl acetate:hexane 100 mg of N-[4-[[4,5-dihydro-2-(2-methylbenzoyl)pyrazolo-[4,3-d]thieno[3,2-b]azepin-6(2H)-yl]carbonyl]phenyl-2-methylbenzamide as a white foam and 200 mg of the product as a white foam.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 18 hours under argon
  2. customThe reaction mixture is evaporated in vacuo to a residue which
  3. dissolutionis dissolved in 40 ml of methylene chloride
  4. washwashed with 20 ml each of water and brine
  5. customThe organic layer is dried (Na2 SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo
  8. customto give a residue which
  9. customis purified by chromatography on silica gel plates by elution with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-481cd7ef1b834670824d898899cfeb1b
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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