Propionic Acid → HCID 178460455, compound

HRID 704756Notes

Reaction equation

HRID 704756 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[C:26]2[C:21](=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH:31]([OH:34])[CH2:32][CH3:33])[C:18]=1[C:35]([NH:37][C:38]1[S:39][CH:40]=[CH:41][N:42]=1)=[O:36].[C:43](O)(=[O:46])[CH2:44][CH3:45].C(NC1CCCCC1)(NC1CCCCC1)=O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[OH:16][C:17]1[C:26]2[C:21](=[C:22]([C:27]([F:29])([F:28])[F:30])[CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH:31]([O:34][C:43](=[O:46])[CH2:44][CH3:45])[CH2:32][CH3:33])[C:18]=1[C:35]([NH:37][C:38]1[S:39][CH:40]=[CH:41][N:42]=1)=[O:36]

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 178458925HCID 178458925, compound

Product 1

HCID 178460455HCID 178460455, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.24 g of dicyclohexylcarbodiimide were added to a suspension of 2 g of 4-hydroxy-2-(1-hydroxypropyl)-N-(2-thiazolyl)-8 trifluoromethyl-3-quinoline carboxamide [prepared as in Step C of Example 10 of Belgian Patent No. 896,941]and 0.4 ml of propionic acid in 20 ml of methylene chloride After stirring for 5 minutes, 0.30 g of 4-dimethylamino-pyridine were added and the mixture stood for an hour with stirring at ambient temperature The dicyclohexylurea formed was filtered off and the organic phase was washed with N hydrochloric acid, then with an aqueous solution of sodium bicarbonate, then with water, followed by drying and concentrating to dryness under reduced pressure The residue was taken up in 15 ml of ether, filtered, dried under reduced pressure to obtain 2.2 g of 4-hydroxy-2-[1-(1-oxopropoxy)-propyl]-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline carboxamide melting at 216° C. which was identical to that obtained in Example 2.

Workup

  1. customprepared as in Step C of Example 10 of Belgian Patent No
  2. waitthe mixture stood for an hour
  3. customformed
  4. filtrationwas filtered off
  5. washthe organic phase was washed with N hydrochloric acid
  6. customby drying
  7. concentrationconcentrating to dryness under reduced pressure The residue
  8. filtrationfiltered
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-df82b5e610714a689ec652af49d9537b
Source dataset
uspto-grants-1991_01
Patent number
US04988708

Reaction notes

Loading…