Sodium hydride → HCID 178424291, compound

HRID 1733995Notes

Reaction equation

HRID 1733995 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 (Na2SO4) 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. dry with materialThe organic layer is dried (Na2SO4)
  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-74123c56015d48a793a855e3a1bc3c28
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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