Diisopropylethylamine → HCID 18672418, 화합물

HRID 1058239노트

반응식

HRID 1058239 반응식
CCN(C(C)C)C(C)C.Cl.[F:11][C:12]1([F:16])[CH2:15][NH:14][CH2:13]1.Br[CH2:18][C:19]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:20]=1[C:21]#[N:22]>C(Cl)Cl>[Cl:27][C:24]1[CH:25]=[CH:26][C:19]([CH2:18][N:14]2[CH2:15][C:12]([F:16])([F:11])[CH2:13]2)=[C:20]([CH:23]=1)[C:21]#[N:22]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 126680522-(Bromomethyl)-5-chlorobenzonitrile

생성물 1

HCID 18672418HCID 18672418, 화합물수율 55.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

DIEA (0.196 mL, 1.12 mmol) was added to a stirred mixture of 3,3-difluoroazetidine hydrochloride (64.8 mg, 0.50 mmol) and 2-bromomethyl-5-chlorobenzonitrile (121.0 mg, 0.52 mmol) in CH2Cl2 (7 mL). After 16 h the reaction was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The residue was partitioned between 1N HCl and ether. The aqueous layer was made neutral with NaHCO3 and was extracted with CH2Cl2. The organic layer was dried with Na2SO4 and then evaporated to give 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile (67.8 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 3.68 (t, J=11.9 Hz. 4H), 3.93 (s, 2H), 7.54 (m, 2H), 7.63 (d, J=2.2 Hz, 1H).

후처리

  1. customAfter 16 h the reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was partitioned between 1N HCl and ether
  6. extractionwas extracted with CH2Cl2
  7. dry with materialThe organic layer was dried with Na2SO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-66db6927a39e435687a3f4545f42d76d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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