Diisopropylethylamine → HCID 67018140, compound

HRID 1671681Notes

Reaction equation

HRID 1671681 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][C@H:3]1[CH2:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[O:18][CH:17]=[CH:16][C:15]=12)=[O:9].CCN(C(C)C)C(C)C.[CH3:28][O:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].CC(=O)OCC.CCCCCCC>CN(C=O)C.CC(=O)OCC>[CH3:28][O:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([N:2]1[CH2:5][CH2:4][C@H:3]1[CH2:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[O:18][CH:17]=[CH:16][C:15]=12)=[O:9])=[O:33]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 889692-Methoxybenzoyl chlorideHCID 21899848Ethylacetate heptaneHCID 67018180HCID 67018180, compound

Product 1

HCID 67018140HCID 67018140, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (5° C.) solution of (2S)-benzofuran-4-carboxylic acid-(azetidine-2-ylmethyl)-amide hydrochloride (10 mg), DIEA (0.015 mL) in dry DMF (0.1 mL), was added portionwise 2-methoxy-benzoyl chloride (7.35 mg). The reaction mixture was stirred at RT for 20 h. The reaction mixture was diluted with EA, washed with water. The organic extract was dried (MgSO4), filtered and concentrated to yield a crude oil. FC (EA/n-heptane: 1/1) gave 7.3 mg (46%) of the title compound as a solid. LC-MS: rt=0.76 min, 365 [M+H]+.

Workup

  1. washwashed with water
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a crude oil

Sources & evidence

ORD record
ord-3a4575c681454595a85b739b103f1ad8
Source dataset
uspto-grants-2011_08
Patent number
US07994336B2

Reaction notes

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