Triethylamine → N-(6-fluoro-1,3-benzothiazol-2-yl)-2,2,3,3-tetramethylcyclopropanecarboxamide

HRID 78410

Reaction equation

HRID 78410 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:41][C:42]1([CH3:50])[C:44]([CH3:46])([CH3:45])[CH:43]1[C:47](O)=[O:48]>CCOC(C)=O.C1COCC1.CCN(CC)CC>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:9][C:47]([CH:43]3[C:44]([CH3:46])([CH3:45])[C:42]3([CH3:50])[CH3:41])=[O:48])[S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acidHCID 3199542-Amino-6-fluorobenzothiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86618903N-(6-fluoro-1,3-benzothiazol-2-yl)-2,2,3,3-tetramethylcyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 68616177Triethylamine tetrahydrofuranSolvent

Procedure

A mixture of 6-fluoro-benzothiazol-2-ylamine (1 equiv), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (1 equiv), 1-hydroxybenzotriazole, triethylamine (1.1 equiv), and 2,2,3,3-tetramethylcyclopropanecarboxylic acid (0.8 equiv) in 3:1 THF/Et3N (1 M) and were stirred overnight at room temperature. The mixture was diluted with EtOAc, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered, and concentrated. Puried by silica gel chromatography afforded the title compound. MS (ESI+) m/z 293 (M+H)+.

Workup

  1. washwashed with 1 M aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-34bf5f0fff8949ce9fdf3d6afcec3606
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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