Dimethylcarbamoyl Chloride → 1,2,3,4-Tetrahydro-6((dimethylamino)carbonyl)oxy-2-N-(3-(2-thienyl)propionyl)isoquinoline

HRID 1088698Notes

Reaction equation

HRID 1088698 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:20])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:6][CH2:5]2.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>N1C=CC=CC=1>[CH3:21][N:22]([CH3:26])[C:23]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:20])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:6][CH2:5]2)=[O:24]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 157187121,2,3,4,-Tetrahydro-6-hydroxy-N-3-(2-thienyl)propionylisoquinoline

Product 1

HCID 157187151,2,3,4-Tetrahydro-6((dimethylamino)carbonyl)oxy-2-N-(3-(2-thienyl)propionyl)isoquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the product of Example 14 (1.5 g) in pyridine (10 mL) at 0° C. was added dropwise dimethyl carbamyl chloride (0.52 mL) and the resulting solution was heated at 70°-80° C. for 24 hours. The pyridine was removed and the reaction diluted with CH2Cl2, washed with water (3x), brine, dried (MgSO4), filtered and concentrated. Chromatography of the residue on silica gel (elution with 1% CH2OH/CH2Cl2) provided 1.29 g of the desired product.

Workup

  1. temperaturethe resulting solution was heated at 70°-80° C. for 24 hours
  2. customThe pyridine was removed
  3. additionthe reaction diluted with CH2Cl2
  4. washwashed with water (3x), brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22103695e1ac40019461d96c5a3a737e
Source dataset
uspto-grants-1990_10
Patent number
US04963563

Reaction notes

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