1,2-Dichloroethane → 4-(4-Chloro-phenyl)-3-[1-[3,5-dimethyl-4-((s)-3-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1839830Notes

Reaction equation

HRID 1839830 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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]([OH:27])=O)[C:20]=2[CH3:28])/[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[N:29]1([CH2:34][C@@H:35]2[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]2)[CH2:33][CH2:32][CH2:31][CH2:30]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1.C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([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]([N:37]4[CH2:38][CH2:39][CH2:40][C@@H:35]([CH2:34][N:29]5[CH2:30][CH2:31][CH2:32][CH2:33]5)[CH2:36]4)=[O:27])[C:20]=2[CH3:28])/[C:11](=[O:17])[NH:12]3)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 600613875-[4-(4-Chloro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 600615084-(4-Chloro-phenyl)-3-[1-[3,5-dimethyl-4-((s)-3-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 55%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[4-(4-Chloro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (112 mg, 0.3 mmol) was coupled with (R)-3-pyrrolidin-1-ylmethyl-piperidine (99 mg, 2 eq.), HOBt (1 eq.), EDC (1.5 eq.) and TEA (3 drops) in THF (1 mL) and acetonitrile (1 mL) at rt for overnight to give 89.5 mg (55%) of the titled compound as a yellow solid.

Sources & evidence

ORD record
ord-ebeaaa7987ac41da83376dc1905b5a49
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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