Methyl iodide → 2-Methylamino-4,5,7,8-tetrahydro-thiazolo(4,5-d)azepine-6-carboxylic acid tert-butyl ester

HRID 400434Notes

Reaction equation

HRID 400434 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][C:14]2[S:17][C:18]([NH2:20])=[N:19][C:13]=2[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:21]I>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][C:14]2[S:17][C:18]([NH:20][CH3:21])=[N:19][C:13]=2[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 84712457Tert-butyl 2-amino-4,5,7,8-tetrahydrothiazolo[5,4-d]azepine-6-carboxylate

Product 1

HCID 866860382-Methylamino-4,5,7,8-tetrahydro-thiazolo(4,5-d)azepine-6-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

104 mg 60% sodium hydrid was added to 700 mg 2-amino-4,5,7,8-tetrahydro-thiazolo (4,5-d) azepine-6-carboxylic acid tert-butyl ester in 1.5 mL THF at 0° C. Then, 162 μL methyliodide was dropped to the mixture. The reaction was stirred over night at RT. The solvent was removed and the residue was purified by HPLC and 121 mg of the desired product was obtained.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-e8648030628a4576bac780fa383e0b1d
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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