Ammonia → HCID 14994964, compound

HRID 1464324Notes

Reaction equation

HRID 1464324 reaction equation
Br[CH:2]([CH3:31])[C:3]([NH:5][C:6]1[S:21][C:9]2[CH2:10][N:11]([C:14]([O:16][CH2:17][CH2:18][C:19]#[CH:20])=[O:15])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])=[O:4].[NH3:32]>C(OCC)(=O)C>[NH2:32][CH:2]([CH3:31])[C:3]([NH:5][C:6]1[S:21][C:9]2[CH2:10][N:11]([C:14]([O:16][CH2:17][CH2:18][C:19]#[CH:20])=[O:15])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14994963HCID 14994963, compound

Product 1

HCID 14994964HCID 14994964, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
100 °C

Procedure

1.16 g of 2-(2-bromopropionylamino)-3-(2-chlorobenzoyl)-6-(3-butynyloxycarbonyl)-4,5,6,7-tetrahydro-thieno[2,3-C]pyridine was dissolved in 36 ml of ethyl acetate, into which ammonia gas was introduced under cooling conditions, followed by heating in a sealed tube at 100° C. After completion of the reaction, the mixture was cooled, to which 50 ml of ethyl acetate was added. The mixture was washed with 1N hydrochloric acid, after which the aqueous phase was neutralized with a sodium carbonate aqueous solution and extracted with chloroform. The resultant organic phase was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced conditions and the resultant residue was purified by the use of silica gel column chromatography (elution solvent: dichloromethane), thereby obtaining 0.36 g of the intended compound.

Workup

  1. additionwas introduced under cooling conditions
  2. customAfter completion of the reaction
  3. additionwas added
  4. washThe mixture was washed with 1N hydrochloric acid
  5. extractionextracted with chloroform
  6. dry with materialThe resultant organic phase was dried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced conditions
  8. customthe resultant residue was purified by the use of silica gel column chromatography (elution solvent: dichloromethane)

Sources & evidence

ORD record
ord-bfefaad4b00846f0a917315784113565
Source dataset
uspto-grants-1994_04
Patent number
US05304553

Reaction notes

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