1,2-Dichloroethane → 1-Benzyl-N3-(3,4-difluorobenzyl)-2-isopropyl-N6-(prop-2-ynyl)-1H-indole-3,6-dicarboxamide

HRID 40091Notes

Reaction equation

HRID 40091 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17](O)=[O:18])[CH:15]=2)[C:10]([C:20](=[O:31])[NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[C:9]1[CH:32]([CH3:34])[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[CH2:39]([NH2:42])[C:40]#[CH:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH:42][CH2:39][C:40]#[CH:41])=[O:18])[CH:15]=2)[C:10]([C:20]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[O:31])=[C:9]1[CH:32]([CH3:34])[CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 239041PropargylamineHCID 250600031-Benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylic Acid2×

Product 1

HCID 597622821-Benzyl-N3-(3,4-difluorobenzyl)-2-isopropyl-N6-(prop-2-ynyl)-1H-indole-3,6-dicarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Following General Procedure G, 1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylic acid (Compound 56, 35 mg, 0.080 mmol) in in CH2Cl2 (3 ml) was added EDC (25 mg, 0.15 mmol) and DMAP (15 mg, 0.09 mmol), followed by propargyl amine (7 mg, 0.09 mmol). The crude material was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as an oil.

Workup

  1. customThe crude material was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-adf3d5177eab43b5b3a3194f36f8525b
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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