Hydrogen Bromide → HCID 59264667, compound

HRID 646408Notes

Reaction equation

HRID 646408 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:16]([NH2:19])([CH3:18])[CH3:17])[N:15]=2)=[CH:7][CH:6]=1)[CH3:2].Br.CN1CCOCC1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:16]([NH:19][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:17])[CH3:18])[N:15]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 7412Benzoyl chlorideHCID 79724-MethylmorpholineHCID 59264669HCID 59264669, compound

Product 1

HCID 59264667HCID 59264667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-[4-(1-Amino-1-methyl-ethyl)-thiazol-2-yl]-benzoic acid ethyl ester:hydrobromide (11.0 mmol) and n-methylmorpholine (2.0 mmol) in dichloromethane (0.10M), add benzoyl chloride (1.0 mmol) diluted in 2 mL dichloromethane. Stir at room temperature for 20 minutes. Wash the reaction with water while extracting with dichloromethane. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify via radial chromatography eluting with ethyl acetate and hexane. MS (m/e): 395.2 (M+H)+

Workup

  1. washWash
  2. customthe reaction with water
  3. extractionwhile extracting with dichloromethane
  4. dry with materialDry the organic layer with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify via radial chromatography
  8. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-742ebb2274b644c9aa1febde9b36bdda
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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