Triethylamine → HCID 67103555, compound

HRID 2079741Notes

Reaction equation

HRID 2079741 reaction equation
[CH3:1][C@@H:2]1[CH2:4][C@H:3]1[C:5](Cl)=[O:6].[NH2:8][C:9]1[S:13][N:12]=[C:11]([Br:14])[C:10]=1[C:15](=[O:17])[CH3:16].C(N(CC)CC)C>ClCCl>[C:15]([C:10]1[C:11]([Br:14])=[N:12][S:13][C:9]=1[NH:8][C:5]([C@@H:3]1[CH2:4][C@H:2]1[CH3:1])=[O:6])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6995697HCID 6995697, compoundHCID 122461921-(5-Amino-3-bromo-1,2-thiazol-4-yl)ethan-1-one

Product 1

HCID 67103555HCID 67103555, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add a freshly prepared 1.93M solution of (1R,2R)-2-methyl-cyclopropanecarbonyl chloride (5.52; mol) in dichloromethane over 15; min to a suspension of 1-(5-amino-3-bromo-isothiazol-4-yl)-ethanone (1.17; kg, 4.93; mol) and triethylamine (859; mL, 6.16; mol) in dichloromethane (5.86; L) at room temperature and stir 4; hours. Quench the reaction with water (1; L) and separate the layers. Dry the organic layer over magnesium sulfate, filter, concentrate and purify the residue by short column silica gel chromatography (3500; g of SiO2) gradient eluting from 100:0; to 40:60 using n-hexane and ethyl acetate to give the title compound as a white solid (1230; g, 82%). MS (m/z): 303, 305; (M+1).

Workup

  1. customQuench
  2. customthe reaction with water (1; L)
  3. customseparate the layers
  4. dry with materialDry the organic layer over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. custompurify the residue by short column silica gel chromatography (3500; g of SiO2) gradient
  8. washeluting from 100:0

Sources & evidence

ORD record
ord-2e3b25e4de6948d98f4584a44670182f
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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