Dimethylformamide → N-{3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}-1-hydroxycyclopropanecarboxamide

HRID 41275Notes

Reaction equation

HRID 41275 reaction equation
[CH3:1][N:2](C)[CH:3]=[O:4].[CH3:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][CH3:16])[CH:11]=[C:10]([O:17][CH3:18])[C:9]=1[C:19]1[N:20]2[N:26]=[C:25]([O:27][CH3:28])C(N)=[C:21]2[S:22][CH:23]=1.C(N=C=N[CH2:35][CH2:36][CH2:37]N(C)C)C.[OH:41]N1C2C=CC=CC=2N=N1>CCCCCCC.C(OCC)(=O)C.O>[CH3:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][CH3:16])[CH:11]=[C:10]([O:17][CH3:18])[C:9]=1[C:19]1[N:20]2[N:26]=[C:25]([O:27][CH3:28])[C:1]([NH:2][C:3]([C:36]3([OH:41])[CH2:37][CH2:35]3)=[O:4])=[C:21]2[S:22][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 579124433-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole-7-amine

Product 1

HCID 67095311N-{3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}-1-hydroxycyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a N,N-dimethylformamide (6 mL) solution of 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole-7-amine (400 mg, 1.14 mmol) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.236 mL, 1.33 mmol) and 1-hydroxybenzotriazole (180 mg, 1.33 mmol), and the mixture was stirred at room temperature over one day and night. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/1 then 1/2) to obtain the title compound (404 mg, 0.93 mmol).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe mixture was filtered
  4. distillationthe solvent in the filtrate was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-21530398d17b4d688e234cdb73de690c
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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