1,2-Dichloroethane → HCID 178465850, compound

HRID 1012128Notes

Reaction equation

HRID 1012128 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[C:18]([O:24][CH2:25][CH3:26])[C:19]([C:21](O)=[O:22])=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5].[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:25]([O:24][C:18]1[C:19]([C:21]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:22])=[CH:20][C:14]2[N:13]=[C:12]([C:8]3[C:7]([NH:6][C:4](=[O:5])[C:3]4[C:2]([F:1])=[CH:30][CH:29]=[CH:28][C:27]=4[F:31])=[CH:11][NH:10][N:9]=3)[NH:16][C:15]=2[CH:17]=1)[CH3:26]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 178465851HCID 178465851, compound

Product 1

HCID 178465850HCID 178465850, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-6-ethoxy-1H-benzimidazole-5-carboxylic acid (50 mg, 0.12 mmol), morpholine (13 μl, 0.14 mmol), EDC (29 mg, 0.15 mmol) and HOBt (21 mg, 0.15 mmol) in DMF (5 mL) was stirred at r.t. for 48 h. The reaction mixture was reduced in vacuo and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, dried (MgSO4) and reduced in vacuo to give the title compound (29 mg) as a gray solid. (LC/MS: Rt 2.56, [M+H]+ 497.03).

Workup

  1. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-f5c614f94226411897f442442f4375cd
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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