Diisopropylethylamine → HCID 86693784, 화합물

HRID 245075

반응식

HRID 245075 반응식
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(C(C)C)CC)(C)C.Cl.[NH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[OH:29]>ClCCl>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]2[OH:29])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 17039400(1S,2R)-2-aminocyclohexan-1-ol hydrochlorideHCID 445509712-Chloro-4-fluoro-3-methylbenzonitrile

생성물 1

HCID 86693784HCID 86693784, 화합물수율 29.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-chloro-4-fluoro-3-methyl-benzonitrile (500 mg, 2.95 mmol), diisopropylethylamine (1.29 mL, 7.37 mmol), and (1S,2R)-2-aminocyclohexanol hydrochloride (670 mg, 4.42 mmol, Acros®) is microwaved using a CEM® microwave at 190° C. for 2 h and 180° C. for 4 h. The mixture is diluted with dichloromethane and washed with 1 N HCl. The aqueous layer is extracted again with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue is purified using radial chromatography, eluting with 2% methanol/dichloromethane. The isolated product is recrystallized with ether and hexane to yield the title compound as a white solid (231 mg, 29%). LC-ES/MS m/z 265.0 (M+1).

후처리

  1. customis microwaved
  2. customat 190° C.
  3. customfor 2 h
  4. washwashed with 1 N HCl
  5. extractionThe aqueous layer is extracted again with dichloromethane
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue is purified
  10. washeluting with 2% methanol/dichloromethane
  11. customThe isolated product is recrystallized with ether and hexane

출처 및 근거

ORD 기록
ord-7392c902ed19404883235588542a6b88
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658693B2

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