N,N'-Dimethylethylenediamine → HCID 86723996, compound

HRID 1475380Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([F:27])=[C:23](Br)[CH:24]=3)[CH2:19][CH2:18]2)=[O:16])[CH2:10][C@H:9]1[CH3:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]1([S:35]([O-:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Na+].CNCCNC>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([F:27])=[C:23]([S:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:37])=[O:36])[CH:24]=3)[CH2:19][CH2:18]2)=[O:16])[CH2:10][C@H:9]1[CH3:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (R)-4-[2-(6-bromo-5-fluoro-2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (0.137 g, 0.30 mmol), sodium phenylsulfinate (0.064 g, 0.39 mmol), copper (1) trifluoromethylsulfonate-benzene complex (0.0045 g, 0.009 mmol), N,N′-dimethylethylenediamine (0.29 g, 0.33 mmol) and dimethyl sulfoxide (1.5 mL) was stirred at 150° C. under nitrogen for 18 h in a sealed vessel. The resulting mixture was partitioned between water (50 mL) and 1:1 Et2O− EtOAc (30 mL) and the organic phase was washed with water (2×20 mL), dried (Na2SO4) and evaporated in vacuo to give a brown oil. Chromatography (SiO2; gradient elution with 0-100% EtOAc in petrol) gave the title compound (0.031 g, ˜25%). MS: [M+H]+=518.

Workup

customThe resulting mixture was partitioned between water (50 mL) and 1:1 Et2O− EtOAc (30 mL)
washthe organic phase was washed with water (2×20 mL)
dry with materialdried (Na2SO4)
customevaporated in vacuo
customto give a brown oil
washChromatography (SiO2; gradient elution with 0-100% EtOAc in petrol)

Sources & evidence

ORD record: ord-7e5b98c07f9f41afaaad4ad5c0dfa9bd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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