1,2-Dichloroethane → HCID 86692738, compound

HRID 1184416Notes

Reaction equation

HRID 1184416 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:9]2[C:15]([OH:17])=O)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([NH2:30])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1.C(=O)=O.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:9]2[C:15]([NH:30][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[C:26]([F:27])([F:28])[F:29])=[O:17])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 280Carbon DioxideHCID 757711-HydroxybenzotriazoleHCID 246932751-(4-Chlorophenyl)-2,2,2-trifluoroethan-1-amineHCID 67124545HCID 67124545, compound

Product 1

HCID 86692738HCID 86692738, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,2R)-2-(4-bromophenyl)-4-oxo-cyclohexane-carboxylic acid (100 mg, 0.300 mmol), 1-(4-chlorophenyl)-2,2,2-trifluoro-ethanamine (the faster eluting enantiomer on AD-H chiral column using MeOH/SF CO2; 62.8 mg, 0.300 mmol) and HOBT (45.9 mg, 0.300 mmol) in CH2Cl2 (5 mL) was reacted with EDC (115 mg, 0.600 mmol) and DMAP (36.6 mg, 0.300 mmol). The reaction was aged at rt until it was complete. The mixture was concentrated and purified on a silica gel column by eluting with 0-50% EtOAc/hexanes to afford the title compound. HPLC/MS: 488.1/490.0 (M+1); Rt=1.19 min (LC-2).

Workup

  1. customwas aged at rt until it
  2. concentrationThe mixture was concentrated
  3. custompurified on a silica gel column
  4. washby eluting with 0-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-4f6a9f9d816d45d591fc7dbe8ebc5472
Source dataset
uspto-grants-2014_03
Patent number
US08669252B2

Reaction notes

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