Triethylamine → HCID 16117681, compound

HRID 1714149Notes

Reaction equation

HRID 1714149 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:22](=[C:23]([CH3:25])[CH:24]=1)[CH2:21][C@H:20]1[C@@H:15]2[CH2:16][NH:17][CH2:18][CH2:19]1.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28].CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:22](=[C:23]([CH3:25])[CH:24]=1)[CH2:21][C@H:20]1[C@@H:15]2[CH2:16][N:17]([CH3:27])[CH2:18][CH2:19]1.[CH2:30]([O:29][C:27]([N:17]1[CH2:16][C@H:15]2[C@H:20]([CH2:21][C:22]3[C:14]2=[CH:13][C:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:7][C:2]=2[Cl:1])=[CH:24][C:23]=3[CH3:25])[CH2:19][CH2:18]1)=[O:28])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16117680HCID 16117680, compound

Product 2

HCID 16117681HCID 16117681, compoundHCID 86611063HCID 86611063, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (8.0 mg, 0.021 mmol) was prepared by following the procedure of example 17. cis-6-(2-Chloro-4-trifluoromethyl-phenyl)-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (16 mg, 0.044 mmol) was reacted with ethyl chloroformate (9.6 mg, 0.088 mmol) and Et3N (22.3 mg, 0.22 mmol) in CH2Cl2 (0.5 mL) to give cis-6-(2-chloro-4-trifluoromethyl-phenyl)-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (12 mg, 0.027 mmol) which was reduced with LiAlH4 (2.1 mg, 0.055 mmol) in THF (1 mL): MS (ES) 380.1 (M+H).

Sources & evidence

ORD record
ord-8b6a3f9db35f46efaea4824b0157d0f1
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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