1,2-Dichloroethane → 2-Methyl-6-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (2-hydroxy-3-pyrrolidin-1-yl-propyl)-amide

HRID 2213562Notes

Reaction equation

HRID 2213562 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2/[C:7](=[C:10]3\[C:11](=[O:24])[NH:12][C:13]4[C:18]\3=[CH:17][C:16]([S:19](=[O:23])(=[O:22])[NH:20][CH3:21])=[CH:15][CH:14]=4)/[CH2:8][CH2:9][C:4]=2[C:3]=1[C:25]([OH:27])=O.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:42][CH2:43][CH:44]([OH:51])[CH2:45][N:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[OH:51][CH:44]([CH2:45][N:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1)[CH2:43][NH:42][C:25]([C:3]1[C:4]2[CH2:9][CH2:8]/[C:7](=[C:10]3/[C:11](=[O:24])[NH:12][C:13]4[C:18]/3=[CH:17][C:16]([S:19](=[O:22])(=[O:23])[NH:20][CH3:21])=[CH:15][CH:14]=4)/[C:5]=2[NH:6][C:2]=1[CH3:1])=[O:27]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 121749931-Amino-3-(pyrrolidin-1-yl)propan-2-olHCID 210515372-Methyl-6-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid

Product 1

HCID 210515502-Methyl-6-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (2-hydroxy-3-pyrrolidin-1-yl-propyl)-amideYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-6-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (Example 5, 78 mg, 0.2 mmol), HOBt (27 mg, 0.2 mmol) and EDC (77 mg, 0.4 mmol) in dry DMF (2 mL) was stirred at room temperature for 30 min. Then 1-amino-3-pyrrolidine-1-yl-propan-2-ol (0.4 mmol) was added and stirring was continued for 48 hours. The solvent was removed under reduced pressure and the residue was crystallized and purified on a silica gel column to give 54 mg of the titled compound as a yellow solid.

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was crystallized
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-2ca8c582745e4fc59dc2b97253a10fd6
Source dataset
uspto-grants-2006_09
Patent number
US07105562B2

Reaction notes

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