Triethylamine → HCID 86629419, compound

HRID 2371211Notes

Reaction equation

HRID 2371211 reaction equation
ClC(OC1C=CC=CC=1)=O.Cl.[Cl:12][C:13]1[S:17][C:16]([NH2:18])=[N:15][CH:14]=1.C(N(CC)CC)C.[C:26]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)(OC(C)(C)C)=[O:27]>C1COCC1.[OH-].[Na+]>[Cl:12][C:13]1[S:17][C:16]([NH:18][C:26]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[O:27])=[N:15][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 1487432-Amino-5-chlorothiazole hydrochloride

Product 1

HCID 86629419HCID 86629419, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Phenyl chloroformate (0.305 mL) was added slowly to a stirring solution of 5-chloro-1,3-thiazol-2-amine hydrochloride (400 mg) in THF (5 mL) containing triethylamine (0.98 mL) under an argon atmosphere. After 1 h N-Boc piperazine was added and the reaction was heated to reflux for 1 h. The reaction mixture was taken up in 1M NaOH (10 mL) and DCM (30 mL) and organic layer was separated and washed with 1 MHCl (aq.) (10 mL). The DCM layer was then dried (MgSO4), filtered and evaporated. Purification by column chromatography 1:4 to 1:1 EtOAc:isohexanes afforded the title compound (278 mg) as a white solid which was used without purification

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 h
  3. customDCM (30 mL) and organic layer was separated
  4. washwashed with 1 MHCl (aq.) (10 mL)
  5. dry with materialThe DCM layer was then dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by column chromatography 1:4 to 1:1 EtOAc

Sources & evidence

ORD record
ord-31715dc2f1c64847ac9e93ea65f8cee4
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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