Hydrochloric Acid → N,N-dimethyl-N'-(6-n-propyl-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonyl)formamidine

HRID 969723노트

반응식

HRID 969723 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:15]([N:18]=[CH:19][N:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=2)[N:7]=1.[Br-].[CH2:24]([Zn+])[CH2:25][CH3:26].O.Cl>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:21][N:20]([CH3:22])[CH:19]=[N:18][S:15]([C:8]1[N:6]2[N:7]=[C:2]([CH2:24][CH2:25][CH3:26])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]([F:14])([F:13])[F:12])(=[O:17])=[O:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 74015820HCID 74015820, 화합물HCID 178455869HCID 178455869, 화합물

생성물 1

HCID 68536680N,N-dimethyl-N'-(6-n-propyl-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonyl)formamidine

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of N′-(6-chloro-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonyl)-N,N-dimethylformamidine (1.00 g, 2.81 mmol) and [1,3-bis(diphenylphosphino)propane]nickel(II) dichloride (0.076 g, 0.14 mmol) in tetrahydrofuran (8.0 ml) was added dropwise a solution of n-propylzinc bromide in tetrahydrofuran (0.5 M, 8.43 ml, 4.22 mmol) with stirring under ice-cooling and nitrogen stream. The reaction mixture was stirred for 30 minutes under ice-cooling and 4.5 hours at room temperature, then poured into cold water and made acid with dilute hydrochloric acid. The precipitated solid was collected by filtration, washed with dilute hydrochloric acid, then water, and purified by silica gel column chromatography (ethyl acetate:chloroform=2:5) to give the title compound as white crystals. The yield was 0.62 g (60.7%).

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 30 minutes under ice-
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with dilute hydrochloric acid
  5. customwater, and purified by silica gel column chromatography (ethyl acetate:chloroform=2:5)

출처 및 근거

ORD 기록
ord-47dc2caa5c5a40d288b9c1333f8cb7cf
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307165B2

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