Diisopropylethylamine → 5-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1426964노트

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HRID 1426964 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11](Cl)=[O:12])=[C:4]2[N:3]=1.CCN(C(C)C)C(C)C.Cl.[Cl:24][CH2:25][CH2:26][NH2:27]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:27][CH2:26][CH2:25][Cl:24])=[O:12])=[C:4]2[N:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 97937372-Chloroethylamine hydrochlorideHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride

생성물 1

HCID 866917475-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 85.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a suspension of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (284 mg, 1.31 mmol) in DCM (10 mL) was added DIEA (1.14 mL, 6.57 mmol). The solution was cooled to 0° C., then treated with 2-chloroethylamine hydrochloride (183 mg, 1.58 mmol) and stirred for 1 hour. The mixture was partitioned between water (30 mL) and DCM (30 mL) and the layers were separated. The aqueous layer was extracted with DCM (2×20 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to afford 5-chloro-N-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (290 mg, 85% yield) as a beige solid. MS (apci) m/z=258.9 (M+H).

후처리

  1. customThe mixture was partitioned between water (30 mL) and DCM (30 mL)
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (2×20 mL)
  4. washthe combined organic phases were washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-42ad6235df2842a0b33c750b51914e3e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933084B2

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