Phosgene → HCID 86759049, compound

HRID 1355652Notes

Reaction equation

HRID 1355652 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([C:25]([O:27][CH3:28])=[O:26])[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)[NH:11][C@@H:10]([CH:22]2[CH2:24][CH2:23]2)[CH2:9]1.[C:38](Cl)([Cl:40])=[O:39]>C1(C)C=CC=CC=1>[F:33][C:32]([F:34])([F:35])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:36])[F:37])[CH:31]=1)[CH2:6][N:7]([C:25]([O:27][CH3:28])=[O:26])[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:38]([Cl:40])=[O:39])[C@@H:10]([CH:22]2[CH2:24][CH2:23]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 86756495HCID 86756495, compound

Product 1

HCID 86759049HCID 86759049, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-cyclopropyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline (Example 102A) (180 mg, 0.33 mmol) in 2 mL of a 1.93M solution of phosgene in toluene was heated to reflux for 1 h. Excess phosgene was removed by purging with nitrogen, and the resulting solution was concentrated to afford the crude title product (208 mg) which was used without further purfication. MS m/z 621 (M+19+); 1H NMR (CDCl3) δ 0.2 (m, 1H), 0.45 (m, 2H), 0.55 (1H), 0.75 (m, 1H).

Workup

  1. temperatureto reflux for 1 h
  2. customExcess phosgene was removed
  3. customby purging with nitrogen
  4. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-e04490a636ec4e85bf0612e019ec13bb
Source dataset
uspto-grants-2003_07
Patent number
US06586448B1

Reaction notes

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