Hydrochloric Acid → HCID 19438742, compound

HRID 1734002Notes

Reaction equation

HRID 1734002 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.[C:23]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24]([C:29](Cl)=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=1.[OH-].[Na+].Cl>O1CCCC1CO>[NH:17]1[C:11]2[C:10]3[S:18][CH:19]=[CH:20][C:9]=3[N:8]([C:6]([C:5]3[CH:21]=[CH:22][C:2]([NH:1][C:29]([C:24]4[C:23]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:30])=[CH:3][CH:4]=3)=[O:7])[CH2:14][CH2:13][C:12]=2[CH:15]=[N:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 19699095HCID 19699095, compound

Product 1

HCID 19438742HCID 19438742, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

As described for Example 2, 6-(4-aminobenzoyl)-1,4,5,6-tetrahydropyrazolo[3,4-d]thieno[3,2-b]azepine (297 mg) is reacted with 0.542 g of [1,1'-biphenyl]-2-carbonyl chloride to give 0.70 g of bis acylated product. A mixture of this product in 13 ml of tetrahydrofuran-methanol (9: 4) and 2.3 ml of 1N NaOH is stirred for 18 hours at room temperature. To the mixture is added 2.3 ml of 1N HCl and the solvent removed. The mixture is triturated with 50 ml of CH2Cl2, filtered and the solid washed with CH2Cl2 and water to give 0.27 g of off-white crystals, m.p. 280°-284° C.

Workup

  1. customto give 0.70 g of bis
  2. customthe solvent removed
  3. customThe mixture is triturated with 50 ml of CH2Cl2
  4. filtrationfiltered
  5. washthe solid washed with CH2Cl2 and water

Sources & evidence

ORD record
ord-7db2d59186b74157952d7aae7ada5fee
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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