Phosgene → HCID 86759047, compound

HRID 1355650Notes

Reaction equation

HRID 1355650 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([C:26]([O:28][CH3:29])=[O:27])[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)[NH:11][C@@H:10]([CH:23]2[CH2:25][CH2:24]2)[CH2:9]1.[C:39](Cl)([Cl:41])=[O:40].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1)[CH2:6][N:7]([C:26]([O:28][CH3:29])=[O:27])[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:39]([Cl:41])=[O:40])[C@@H:10]([CH:23]2[CH2:24][CH2:25]2)[CH2:9]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 19083224Phosgen tolueneHCID 86759046HCID 86759046, compound

Product 1

HCID 86759047HCID 86759047, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-8-bromo-2-cyclopropyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline (Example 100C) (1.0 g) in 50 mL of a 20% phosgene in toluene solution was heated to reflux for 24 h. Additional phosgene/toluene (50 ml) was added and heating was continued for an additional 24 h. Excess phosgene was removed by purging with nitrogen. The resulting solution was concentrated to afford the crude title product which was used without further purification. MS m/z 681.5 (M+).

Workup

  1. temperatureto reflux for 24 h
  2. temperatureheating
  3. customExcess phosgene was removed
  4. customby purging with nitrogen
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-d0155d3a07154ab989e58f6bafed6a92
Source dataset
uspto-grants-2003_07
Patent number
US06586448B1

Reaction notes

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