1,2-Dichloroethane → 3-[1-(4-{(s)-2-[(Cyclopropylmethyl-amino)-methyl]-pyrrolidine-1-carbonyl}-3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

HRID 1839819Notes

Reaction equation

HRID 1839819 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:23][C:22]([CH3:24])=[C:21]([C:25](O)=[O:26])[C:20]=2[CH3:28])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH:43]1([CH2:46][NH:47][CH2:48][C@@H:49]2[CH2:53][CH2:52][CH2:51][NH:50]2)[CH2:45][CH2:44]1>CN(C=O)C.C(Cl)Cl>[CH:43]1([CH2:46][NH:47][CH2:48][C@@H:49]2[CH2:53][CH2:52][CH2:51][N:50]2[C:25]([C:21]2[C:20]([CH3:28])=[C:19](/[CH:18]=[C:10]3\[C:11](=[O:17])[NH:12][C:13]4[C:9]\3=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[CH:16]=[CH:15][CH:14]=4)[NH:23][C:22]=2[CH3:24])=[O:26])[CH2:44][CH2:45]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 69741373Cyclopropylmethyl-(s)-1-pyrrolidin-2-ylmethyl-amineHCID 697413865-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 599896433-[1-(4-{(s)-2-[(Cyclopropylmethyl-amino)-methyl]-pyrrolidine-1-carbonyl}-3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (70 mg, 0.185 mmol), EDC (70 mg, 0.37 mmol), HOBt (26 mg, 0.19 mmol) in DMF (4 mL) was added TEA (0.08 mL) and cyclopropylmethyl-(S)-1-pyrrolidin-2-ylmethyl-amine (0.05 mL, 0.37 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-54af316cf8a645caa8e94b7e2fa8a9c1
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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