Toluene → HCID 86755978, compound

HRID 369917Notes

Reaction equation

[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=2)[C@H:9]([NH:20][CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[CH2:8][C@@H:7]1[CH3:36])=[O:5])[CH3:2].C1(C)C=CC=CC=1.[C:44](Cl)([Cl:46])=[O:45]>>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:17])([F:18])[F:19])=[CH:13][CH:14]=2)[C@H:9]([N:20]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[C:24]([C:32]([F:35])([F:33])[F:34])[CH:23]=2)[C:44]([Cl:46])=[O:45])[CH2:8][C@@H:7]1[CH3:36])=[O:5])[CH3:2]

Participants

Reactant 3

HCID 1140Toluene

HCID 6371Phosgene

HCID 86755979HCID 86755979, compound

Product 1

HCID 86755978HCID 86755978, compoundYield 76%

Procedure

cis-4-((3,5-Bis-trifluoromethyl-benzyl)-amino]-2-methyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (prepared in a manner analogous to the procedures described for Examples 3A-3E) (146 mg, 0.28 mmol) was dissolved in 2 mL of a 1.93M phosgene solution in toluene (3.9 mmol). After heating at reflux for 1.5 h, the sample was concentrated in vacuo to afford the title product (125 mg, 76%). 1H NMR (CDCl3) δ 1.2-1.6 (m, 7H), 2.2-2.4 (m, 1H), 4.2-4.6 (m, 4H), 5.2-5.6 (m, 2H), 7.1 (s, 1H), 7.5-7.9 (m, 5H).

Workup

temperatureAfter heating
temperatureat reflux for 1.5 h
concentrationthe sample was concentrated in vacuo

Sources & evidence

ORD record: ord-c41d36e0f0f947edb2b7a80251db3fa3
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140343

Reaction notes

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