Tetrahydrofuran → HCID 178453118, compound

HRID 980226Notes

Reaction equation

HRID 980226 reaction equation
[O:1]=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[NH:22][C:23](=O)[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:3][C:4](=[O:11])[NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1.O1CCCC1>CN(C)C1C=CN=CC=1.O>[OH:1][C:2]1[C:12]2[C:13](=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:16][CH:17]=2)[N:22]=[C:23]([CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[C:3]=1[C:4]([NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1)=[O:11]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 13578786HCID 13578786, compound

Product 1

HCID 178453118HCID 178453118, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

7.3 g of the product of Step B, 140 ml of tetrahydrofuran and 2.4 g of 4-dimethylamino-pyridine were stirred for 1 hour at ambient temperature and the solvent was eliminated under reduced pressure. The residue was taken up in 100 ml of water and 20 ml of N hydrochloric acid and the solution was extracted with a mixture of ethyl acetate and tetrahydrofuran. After washing the organic phase with water and drying and concentrating the filtrate under reduced pressure, 7 g of crude product were obtained which was triturated in ether, separated, washed with ether and dried under reduced pressure at 60° C. to obtain 6.6 g of 1,1-dimethylethyl N-[[4-hydroxy-8-(trifluoromethyl)-3-[(2-thiazolylamino)-carbonyl]quinolin-2-yl]-methyl]-carbamate melting at 238° C.

Workup

  1. extraction20 ml of N hydrochloric acid and the solution was extracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washAfter washing the organic phase with water
  3. customdrying
  4. concentrationconcentrating the filtrate under reduced pressure
  5. custom7 g of crude product were obtained which
  6. customwas triturated in ether
  7. customseparated
  8. washwashed with ether
  9. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-8895db0111e841f6b8b692e44ea3864d
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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