Ammonia → HCID 14986622, compound

HRID 129492Notes

Reaction equation

HRID 129492 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([C:19](=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[C:11]([NH:13][C:14](=[O:18])[CH:15](Br)[CH3:16])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[NH3:28]>ClC(Cl)C.C(OCC)(=O)C>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([C:19](=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[C:11]([NH:13][C:14](=[O:18])[CH:15]([NH2:28])[CH3:16])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 14986621HCID 14986621, compound

Product 1

HCID 14986622HCID 14986622, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

841 g of 6-acetyl-2-(2-bromopropionylamino)-3-(2-chlorobenzoyl)-4,5,6,7-tetrahydro-thieno[2,3-C]pyridine was dissolved in 0.72 liters of dichloroethane and 1.08 liters of ethyl acetate, into which ammonia gas was introduced at -10° C. The mixture was subjected to reaction in an autoclave at 100° C. for 1 hour. After completion of the reaction, excess ammonia gas was removed and the reaction solution was poured into 3N HCl under ice-cooling conditions. After extraction with ethylacetate, the aqueous phase was neutralized with a saturated sodium carbonate aqueous solution, followed by repeating extraction with chloroform. The resultant organic phase was washed with a saturated saline solution, followed by drying with anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure to obtain 636.8 g of the intended compound.

Workup

  1. customThe mixture was subjected to reaction in an autoclave at 100° C. for 1 hour
  2. customwas removed
  3. additionthe reaction solution was poured into 3N HCl under ice-
  4. temperaturecooling conditions
  5. extractionAfter extraction with ethylacetate
  6. extractionextraction with chloroform
  7. washThe resultant organic phase was washed with a saturated saline solution
  8. dry with materialby drying with anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-eaa27070b0a74cde8ef1df2afa429fec
Source dataset
uspto-grants-1995_11
Patent number
US05468740

Reaction notes

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