2-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-thiazolyl)benzene-propanamide → HCID 178434921, compound

HRID 1982600Notes

Reaction equation

HRID 1982600 reaction equation
Cl[CH:2]([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:22])[CH2:13][C:14]([NH:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1)=[O:15])=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:23][CH:2]1[C:3]2=[N:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:12]([OH:22])=[C:13]2[C:14](=[N:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[O:15]1

Participants

4

Reactant 1

HCID 134230852-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-thiazolyl)benzene-propanamide

Product 1

HCID 178434921HCID 178434921, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7 g of the product of Step B, 50 ml of tetrahydrofuran and 2.92 g of 4-dimethylamino-pyridine was refluxed for 24 hours and was cooled to room temperature and iced and vacuum filtered. The product was washed with tetrahydrofuran and dried under reduced pressure at 90° C. The product was stirred with 100 ml of water at room temperature and was vacuum filtered. The product was washed with water and dried under reduced pressure at 90° C. to obtain 3.5 g of 1,3-dihydro-3-methyl-1-(2-thiazolylimino)-furo[3,4-b]quinoline-9-ol melting at >270° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationiced and vacuum filtered
  3. washThe product was washed with tetrahydrofuran
  4. customdried under reduced pressure at 90° C
  5. filtrationfiltered
  6. washThe product was washed with water
  7. customdried under reduced pressure at 90° C.

Sources & evidence

ORD record
ord-3c16362e66d94a1f8f948d364f2bd2e7
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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