3-Chloro-4-formylbenzonitrile → tert-Butyl (2-Chloro-4-cyanophenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate

HRID 517222Notes

Reaction equation

HRID 517222 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][C:18]2[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]=2[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:5](C)[CH:4]=1)#[N:2].[Cl:37]C1C=C(C=CC=1C=O)C#N>>[Cl:37][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[N:9]([CH2:17][C:18]1[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]=1[NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 122905503-Chloro-4-formylbenzonitrileHCID 86732339tert-Butyl (4-Cyano-2-methylphenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate2×

Product 1

HCID 86732342tert-Butyl (2-Chloro-4-cyanophenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate

Procedure

The title compound is prepared in analogy to tert-butyl (4-cyano-2-methylphenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate (intermediate 51), using 3-chloro-4-formylbenzonitrile (500 mg, 6.04 mmol) as starting material. Yield: 1.05 g; ESI mass spectrum [M+H]+=520; Retention time HPLC: 0.81 min (X012_S01).

Workup

  1. custom0.81 min (X012_S01)

Sources & evidence

ORD record
ord-83c9430a9dc34803b0e1ee5517c85ba4
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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