1,2-Dichloroethane → HCID 59077640, compound

HRID 1359838Notes

Reaction equation

HRID 1359838 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]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH:49]1([NH:52][CH2:53][C@H:54]2[NH:58][CH2:57][C@H:56]([OH:59])[CH2:55]2)[CH2:51][CH2:50]1>CN(C=O)C.C(Cl)Cl>[CH:49]1([NH:52][CH2:53][C@@H:54]2[CH2:55][C@@H:56]([OH:59])[CH2:57][N:58]2[C:31](=[O:32])[CH2:30][C:26]2[C:25]([CH3:34])=[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:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:12])=[O:11])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])[CH2:51][CH2:50]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 59077497HCID 59077497, compoundHCID 69870158HCID 69870158, compound

Product 1

HCID 59077640HCID 59077640, compoundYield 17.2%

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-pyrrol-3-yl}-acetic acid (238 mg, 0.46 mmol), HOBt (69 mg, 1.2 eq.) and EDC (105 mg, 1.2 eq.) in DMF (8 mL) was added TEA (69 mg, 2.5 eq.) and (3R,5S)-5-cyclopropylaminomethyl-pyrrolidin-3-ol (312 mg, 4 eq.). After stirring at rt for 1 day, the reaction was diluted with DCM (200 mL), washed with ammonium chloride solution, sodium bicarbonate and brine, dried and concentrated. The residue was purified on a silica gel column to give 52 mg of the titled compound as a yellow solid.

Workup

  1. washwashed with ammonium chloride solution, sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-558baaf2665941e5affc222940cf707f
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

Loading…