tert-Butanol → [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester

HRID 1826957

반응식

HRID 1826957 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16](C(O)=O)[N:17]([CH3:19])[N:18]=[C:11]12.[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24].C([N:30]([CH2:33]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1>C(OCC)(=O)C.CCCCCC>[C:23]([O:27][C:33](=[O:42])[NH:30][C:16]1[N:17]([CH3:19])[N:18]=[C:11]2[C:12]=1[CH2:13][CH2:14][CH2:15][N:10]2[C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1])([CH3:26])([CH3:25])[CH3:24]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 221362637-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

생성물 1

HCID 23527225[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

A 159 mg sample of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid was combined with 2.5 mL of t-butanol and 140 μL of triethylamine was added. Then 129 μL of diphenylphosphoryl azide was added and the reaction mixture was heated to 85° C. for 2 h. After cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with 1M aqueous sodium bisulfate, aqueous sodium bicarbonate, water, and brine. The ethyl acetate solution was dried with magnesium sulfate and concentrated to give material which was chromatographed on silica gel eluting with an acetone/hexane gradient. Product containing fractions were concentrated to give a solid residue which was slurried in a small amount of boiling hexane. After the mixture cooled to room temperature, the solids were collected by filtration to provide 71 mg of [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester, mp 171.4–175.7° C.

후처리

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. washwashed with 1M aqueous sodium bisulfate, aqueous sodium bicarbonate, water, and brine
  4. dry with materialThe ethyl acetate solution was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customto give material which
  7. customwas chromatographed on silica gel eluting with an acetone/hexane gradient
  8. additionProduct containing fractions
  9. concentrationwere concentrated
  10. customto give a solid residue which
  11. temperatureAfter the mixture cooled to room temperature
  12. filtrationthe solids were collected by filtration

출처 및 근거

ORD 기록
ord-6c0b07c2bca540e6b00a3aaacc1369e5
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053103B2

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