Isopropanol → HCID 86759048, compound

HRID 1355651Notes

Reaction equation

HRID 1355651 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([C:29]([O:31][CH3:32])=[O:30])[C@H:8]1[C:17]2[C:12](=[C:13]([Br:22])[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=2)[N:11]([C:23](Cl)=[O:24])[C@@H:10]([CH:26]2[CH2:28][CH2:27]2)[CH2:9]1.[CH:42]([OH:45])([CH3:44])[CH3:43]>>[CH:42]([O:45][C:23]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:13]=2[Br:22])[C@H:8]([N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:40])([F:41])[F:1])[CH:35]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:33]=2)[C:29]([O:31][CH3:32])=[O:30])[CH2:9][C@@H:10]1[CH:26]1[CH2:28][CH2:27]1)=[O:24])([CH3:44])[CH3:43]

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 86759047HCID 86759047, compound

Product 1

HCID 86759048HCID 86759048, compound

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-8-bromo-2-cyclopropyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carbonyl chloride (Example 100D) (1.5 g) in isopropanol was heated to reflux for 48 h. The reaction was cooled and concentrated, and the residue was chromatographed (5-10% EtOAc/hexane) to afford the title product (1.0 g). MS m/z 705.4 (M+); 1H NMR (CDCl3) δ 3.8 (s, 3H), 7.1 (s, 1 H), 7.8 (s, 2H).

Workup

  1. temperatureto reflux for 48 h
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customthe residue was chromatographed (5-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-04d17ee4796f40b3952e82bc06ac4e9a
Source dataset
uspto-grants-2003_07
Patent number
US06586448B1

Reaction notes

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