Hydrochloric Acid → HCID 178495126, compound

HRID 704751Notes

Reaction equation

HRID 704751 reaction equation
[Cl:1][CH:2]([CH2:27][O:28][CH3:29])[C:3]([NH:5][C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:9]=[CH:8][C:7]=1[C:16](=[O:26])[CH2:17][C:18]([NH:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=[O:19])=O.O1CCCC1.Cl>CN(C)C1C=CN=CC=1.O>[Cl:1][CH:2]([C:3]1[C:17]([C:18]([NH:20][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[O:19])=[C:16]([OH:26])[C:7]2[C:6](=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:9][CH:8]=2)[N:5]=1)[CH2:27][O:28][CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13785627HCID 13785627, compound

Product 1

HCID 178495126HCID 178495126, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 33.35g of the product of Step A, 10g of 4-dimethylamino-pyridine and 300ml of tetrahydrofuran was refluxed for 30 minutes and was then cooled to room temperature and poured into a mixture of water and 2N hydrochloric acid. The mixture was extracted with ethyl acetate and the organic phase was washed, dried and evaporated to dryness. The residue was empasted with ether, vacuum filtered, washed and dried under reduced presssure at 60° C. to obtain 28.2g of 2-(1-chloro-2-methoxyethyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline carboxamide melting at 186° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed
  4. customdried
  5. customevaporated to dryness
  6. filtrationfiltered
  7. washwashed
  8. customdried
  9. customat 60° C.

Sources & evidence

ORD record
ord-f7b38d1ef521469c894cdad44b1c5702
Source dataset
uspto-grants-1991_01
Patent number
US04988708

Reaction notes

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