tert-Butanol → Tert-butyl (6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate

HRID 1971783노트

반응식

HRID 1971783 반응식
[CH3:1][O:2][C:3]1[C:10](C(O)=O)=[C:6]2[S:7][CH:8]=[CH:9][N:5]2[N:4]=1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>O1CCOCC1>[CH3:1][O:2][C:3]1[C:10]([NH:16][C:19](=[O:28])[O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[C:6]2[S:7][CH:8]=[CH:9][N:5]2[N:4]=1

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471Triethylamine2회HCID 199401P,P-Diphenylphosphinic azideHCID 670951146-Methoxypyrazolo[5,1-b]thiazole-7-carboxylic acid

생성물 1

HCID 57912437Tert-butyl (6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate수율 35.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a mixture of 6-methoxypyrazolo[5,1-b]thiazole-7-carboxylic acid (300 mg, 1.51 mmol) and 1,4-dioxane (4 mL) were added triethylamine (0.215 mL, 1.54 mmol) and diphenylphosphoryl azide (0.325 mL, 1.51 mmol) while stirring at room temperature, and the mixture was stirred and heated to reflux for 3 hour. After returning the mixture to room temperature, triethylamine (0.631 mL, 4.53 mmol) and tert-butanol (0.289 mL, 3.02 mmol) were added and the mixture was stirred and heated to reflux for 3 hour. After returning the mixture to room temperature, the solvent in the mixture was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/4) to obtain the title compound (144 mg, 0.535 mmol).

후처리

  1. stirringthe mixture was stirred
  2. temperatureheated
  3. temperatureto reflux for 3 hour
  4. customto room temperature
  5. stirringthe mixture was stirred
  6. temperatureheated
  7. temperatureto reflux for 3 hour
  8. customto room temperature
  9. distillationthe solvent in the mixture was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/4)

출처 및 근거

ORD 기록
ord-be7a4a4dee7c42d5bb5b1889f6636f31
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431603B2

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