Methylamine → Carbamic acid, N-[4-[(methylamino)carbonyl]-1,2,3-thiadiazol-5-yl]-, 1,1-dimethylethyl ester

HRID 467679Notes

Reaction equation

HRID 467679 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[N:11][C:10]=1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.CN>CN(C=O)C>[CH3:17][NH:18][C:14]([C:10]1[N:11]=[N:12][S:13][C:9]=1[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70116272HCID 70116272, compound

Product 1

HCID 70115888Carbamic acid, N-[4-[(methylamino)carbonyl]-1,2,3-thiadiazol-5-yl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-tert-butoxycarbonylamino-[1,2,3]thiadiazole-4-carboxylic acid (0.66 g, 2.7 mmol) in DMF (10 ml) was treated with TBTU (1.16 g, 3.5 mmol), N,N-diisopropyl ethyl amine (2.29 ml, 13.5 mmol) and methylamine (1.75 ml, 2M THF solution) and stirred at ambient temperature for 5 h. The reaction mixture was partitioned between potassium hydrogen sulfate (30 ml, 10% aqueous solution) and ethyl acetate (60 ml) and extracted. The organic layer was washed with water and brine, and the aqueous phases were back-extracted with ethyl acetate. The combined organic phases were dried and the solvent was evaporated. The residue was suspended in dichloromethane, sucked off, and the filtrate was evaporated. The product was obtained after purification of the crude material by silica gel chromatography using a heptane/ethyl acetate gradient as colorless solid (0.23 g, 33%).

Workup

  1. customThe reaction mixture was partitioned between potassium hydrogen sulfate (30 ml, 10% aqueous solution) and ethyl acetate (60 ml)
  2. extractionextracted
  3. washThe organic layer was washed with water and brine
  4. extractionthe aqueous phases were back-extracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. customthe solvent was evaporated
  7. customthe filtrate was evaporated
  8. customThe product was obtained
  9. customafter purification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-512f283ee4b24a93a4703055f7dcf886
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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