1,2-Dichloroethane → HCID 60061360, compound

HRID 1839832Notes

Reaction equation

HRID 1839832 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:21]([CH3:27])=[CH:22][C:23]=2[C:24](O)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[F:42][C:43]([F:50])([F:49])[CH2:44][NH:45][CH2:46][CH2:47][NH2:48]>CN(C=O)C>[F:42][C:43]([F:50])([F:49])[CH2:44][NH:45][CH2:46][CH2:47][NH:48][C:24]([C:23]1[CH:22]=[C:21]([CH3:27])[NH:20][C:19]=1/[CH:18]=[C:10]1\[C:11](=[O:17])[NH:12][C:13]2[C:9]\1=[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH:16]=[CH:15][CH:14]=2)=[O:25]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 18179872HCID 18179872, compoundHCID 697405872-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z) ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 60061360HCID 60061360, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (53 mg, 0.15 mmol), HOBt (28 mg), EDC (36 mg), TEA (0.042 mL) and N1-(2,2,2-trifluoro-ethyl)-ethane-1,2-diamine (0.036 mL) in DMF (1 mL) was stirred at rt for 48 hours. The solvent was removed and diluted with sat. NaHCO3. It was then extracted with DCM, dried and concentrated. The residue was purified on a silica gel column to give 52 mg (71%) of the titled compound.

Workup

  1. customThe solvent was removed
  2. additiondiluted with sat. NaHCO3
  3. extractionIt was then extracted with DCM
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-62df405356be4cdb8a6d6c76b61b688c
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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