1,2-Dichloroethane → HCID 60061264, compound

HRID 1839835Notes

Reaction equation

HRID 1839835 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:20]C(C)=[CH:22][C:23]=2[C:24](O)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.[CH2:28](Cl)[CH2:29]Cl.[CH:32]1[CH:33]=[CH:34][C:35]2[N:40](O)N=[N:38][C:36]=2C=1>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:20][C:28]([CH3:29])=[CH:22][C:23]=2[C:24]([N:40]2[CH2:32][CH2:33][CH2:34][C@H:35]2[CH2:36][N:38]2[CH2:6][CH2:7][C@H:2]([F:1])[CH2:3]2)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 697405872-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z) ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 60061264HCID 60061264, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (100 mg, 0.28 mmol), EDC (115 mg, 0.3 mmol), HOBt (40 mg, 0.3 mmol) in DMF (4 mL) was added TEA (0.14 mL) and (S)-3-fluoro-1-(S)-1-pyrrolidin-2-ylmethyl-pyrrolidine (100 mg, 0.58 mmol). The mixture was stirred at rt for 20 hours, The reaction was diluted with DCM, washed with water, NaHCO3, dried and concentrated. The residue was purified on a silica gel column to give the titled compound.

Workup

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

Sources & evidence

ORD record
ord-6de0ff08946047aeb0bfc0e5880286aa
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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