1,2-Dichloroethane → HCID 59077651, compound

HRID 1359818Notes

Reaction equation

HRID 1359818 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([C:30]([OH:32])=O)[C:25]=1[CH3:33])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH:48]1([NH:51][C:52]([C@@H:54]2[CH2:58][C@@H:57]([OH:59])[CH2:56][NH:55]2)=[O:53])[CH2:50][CH2:49]1>CN(C=O)C.C(Cl)Cl>[CH:48]1([NH:51][C:52]([C@@H:54]2[CH2:58][C@@H:57]([OH:59])[CH2:56][N:55]2[C:30]([C:26]2[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]3\[C:17](=[O:22])[NH:18][C:19]4[C:15]\3=[CH:14][C:13]([S:10]([CH2:9][C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])(=[O:11])=[O:12])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])=[O:32])=[O:53])[CH2:50][CH2:49]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 28943488HCID 28943488, compoundHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 59077651HCID 59077651, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (232 mg, 0.46 mmol), HOBt (68 mg, 0.51 mmol) and EDC (105 mg, 0.55 mmol) in DMF (8 mL) was added (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamide (excess) and TEA (0.95 mL, 0.6 mmol). The mixture was stirred at rt for 3 days. The reaction was diluted with DCM (200 mL), washed with NH4Cl, NaHCO3, brine, dried and concentrated. The residue was purified on a silica gel column to give 92 mg of the titled compound. MS m/z 671 [M−1].

Workup

  1. washwashed with NH4Cl, NaHCO3, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-c2465d88b3734f0cb47fb7692b994348
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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