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Pyridine → 2-(2-(Tert-butyldimethylsilyloxy)-2-methylpropyl)-4-(5-chloro-2-methoxyphenyl)thiazol-5-amine

HRID 1466670
Notes
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Reaction equation

HRID 1466670 reaction equation
[NH2:1][C:2](=O)[CH:3]([NH:13][C:14](=O)[CH2:15][C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])([CH3:18])[CH3:17])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1.N1C=CC=CC=1>C(Cl)Cl>[Si:20]([O:19][C:16]([CH3:18])([CH3:17])[CH2:15][C:14]1[S:38][C:2]([NH2:1])=[C:3]([C:4]2[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=2[O:11][CH3:12])[N:13]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 87949Lawesson's reagentHCID 66847283N-(2-amino-1-(5-chloro-2-methoxyphenyl)-2-oxoethyl)-3-(tert-butyldimethylsilyloxy)-3-methylbutanamide

Product 1

HCID 668473132-(2-(Tert-butyldimethylsilyloxy)-2-methylpropyl)-4-(5-chloro-2-methoxyphenyl)thiazol-5-amineYield 33%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of N-(2-amino-1-(5-chloro-2-methoxyphenyl)-2-oxoethyl)-3-(tert-butyldimethylsilyloxy)-3-methylbutanamide (327 mg, 0.76 mmol), Lawesson's reagent (308 mg, 0.76 mmol) and pyridine (2.5 mL) was heated to 95° C. for 18 hours. DCM was added, the organics washed with sodium hydrogen carbonate (sat. aq.) and brine, then evaporated to dryness. The residues were purified by flash chromatography on silica gel (DCM) to afford 107 mg (33%) of 2-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-(5-chloro-2-methoxyphenyl)thiazol-5-amine LCMS (ESI) m+H=427.3.

Workup

  1. washthe organics washed with sodium hydrogen carbonate (sat. aq.) and brine
  2. customevaporated to dryness
  3. customThe residues were purified by flash chromatography on silica gel (DCM)

Sources & evidence

ORD record
ord-51ec62992efe4bf8990a0905523c86df
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999998B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes