2,2,2-Trifluoroethanol → HCID 86759763, compound

HRID 1071712Notes

Reaction equation

HRID 1071712 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]([C:28]([O:30][CH3:31])=[O:29])[C@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=2)[N:11]([C:22](Cl)=[O:23])[C@@H:10]([CH:25]2[CH2:27][CH2:26]2)[CH2:9]1.[F:41][C:42]([F:46])([F:45])[CH2:43][OH:44]>>[F:41][C:42]([F:46])([F:45])[CH2:43][O:44][C:22]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[C@H:8]([N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:40])([F:39])[F:1])[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=2)[C:28]([O:30][CH3:31])=[O:29])[CH2:9][C@@H:10]1[CH:25]1[CH2:26][CH2:27]1)=[O:23]

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 86759049HCID 86759049, compound

Product 1

HCID 86759763HCID 86759763, compoundYield 77%

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-cyclopropyl-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carbonyl chloride (Example 102B) (20 mg) in 2,2,2-trifluoroethanol (5 mL) was heated to reflux. After 1 h, the reaction was cooled and concentrated, and the residue was chromatographed (5-10% EtOAc/hexane) to afford the title product (22 mg, 77%). MS m/z 685 (M++19); 1H NMR (CDCl3) δ 3.82 (s, 3H), 7.17 (C5, s, 1H).

Workup

  1. temperaturethe reaction was cooled
  2. concentrationconcentrated
  3. customthe residue was chromatographed (5-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-b84861f2ec464881936ce5cc3587b942
Source dataset
uspto-grants-2005_06
Patent number
US06906082B2

Reaction notes

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