1,2-Dichloroethane → HCID 178469043, compound

HRID 1951442Notes

Reaction equation

HRID 1951442 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]([OH:14])=O)=[N:9][NH:10][CH:11]=1)=[O:5].C(Cl)CCl.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32](O)N=N[C:28]=2[CH:29]=1.[CH3:34][CH2:35][O:36][C:37](C)=[O:38]>CN(C=O)C>[CH2:35]([O:36][C:37]([CH:24]1[CH2:29][CH2:28][CH:27]([NH:32][C:12]([C:8]2[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:2]=3[F:1])=[CH:11][NH:10][N:9]=2)=[O:14])[CH2:26][CH2:25]1)=[O:38])[CH3:34]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 178524954HCID 178524954, compound

Product 1

HCID 178469043HCID 178469043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the ethyl ester (103 mg, 0.60 mmol), 4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (134 mg, 0.50 mmol), EDC (115 mg, 0.60 mmol) and HOBt (81 mg, 0.60 mmol) in DMF (5 ml) was stirred at ambient temperature for 16 hours. The mixture was reduced in vacuo, the residue taken up in EtOAc and washed successively with saturated aqueous sodium bicarbonate, water and brine. The organic portion was dried (MgSO4) and reduced in vacuo to give 4-{[4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carbonyl]-amino}-cyclohexanecarboxylic acid ethyl ester (112 mg).

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate, water and brine
  2. dry with materialThe organic portion was dried (MgSO4)

Sources & evidence

ORD record
ord-0abf1d838f93412b8639ead6af997cab
Source dataset
uspto-grants-2013_03
Patent number
US08404718B2

Reaction notes

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