Triethylamine → HCID 20616913, compound

HRID 2119599Notes

Reaction equation

HRID 2119599 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([N:16]=[C:17](N)[CH3:18])=[S:15])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24](=[O:27])[CH2:25]Br.CCN(CC)CC>C(O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[S:15][C:25]([C:24](=[O:27])[C:23]2[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=2[CH3:21])=[C:17]([CH3:18])[N:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 124306762-Bromo-2'-methylacetophenoneHCID 73686214{5-[3-(1-Amino-ethylidene)-thioureido]-pentyl}-carbamic acid tert-butyl ester

Product 1

HCID 20616913HCID 20616913, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 290 mg (0.96 mmol) {5-[3-(1-Amino-ethylidene)-thioureido]-pentyl}-carbamic acid tert-butyl ester in 5 ml ethanol was added 213 mg (1 mmol) o-Methylphenacyl bromide and 139 μl NEt3 and allowed to stir for 5 h at room temperature. Afterwards the mixture was directly applied to preparative HPLC on reversed phase eluting with an acetonitrile/water gradient. The evaporation of the product fractions yielded 180 mg (45%) of the title compound.

Workup

  1. washeluting with an acetonitrile/water gradient
  2. customThe evaporation of the product fractions

Sources & evidence

ORD record
ord-cf2d6914c371415394b7cc0b63c3e7eb
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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