Triethylamine → 5-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline

HRID 633478

반응식

HRID 633478 반응식
[BH4-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([S:13][C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].ClC1N2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH:24]=[CH:25][C:20]2=[N:19][N:18]=1.C(N(CC)CC)C>CN(C)C=O.O>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]3[N:15]([C:14]([S:13][C:6]4[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH:5]=4)[NH2:3])=[N:18][N:19]=3)[N:22]=2)=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 866478753-Amino-4-nitrophenyl thiocyanate

생성물 1

HCID 675246885-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline수율 31.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

342 mg of sodium borohydride are added to a mixture of 1.76 g of commercial 3-amino-4-nitrophenyl thiocyanate in 15 cm3 of N,N-dimethylformamide. The reaction is stirred at ambient temperature for 2 h and then 746 mg of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine and 1.25 cm3 of triethylamine are added. The resulting mixture is then heated to 95° C. and then stirred for 1 h at 20° C. After the addition of demineralized water, the mixture obtained is extracted with 3×100 cm3 of ethyl acetate (a small amount of methanol is added due to solubility problems). The organic phases are combined and then dried over magnesium sulphate and concentrated to dryness, so as to give a brown solid which is chromatographed on a 25 g Merck cartridge of silica 15-40 μm (elution with ethyl acetate). 360 mg of 5-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline are thus obtained in the form of a green solid, the characteristics of which are as follows:

후처리

  1. temperatureThe resulting mixture is then heated to 95° C.
  2. stirringstirred for 1 h at 20° C
  3. customthe mixture obtained
  4. extractionis extracted with 3×100 cm3 of ethyl acetate (a small amount of methanol
  5. additionis added due to solubility problems)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness
  8. customso as to give a brown solid which
  9. customis chromatographed on a 25 g Merck cartridge of silica 15-40 μm (elution with ethyl acetate)

출처 및 근거

ORD 기록
ord-becfe698d8c8491297238273c7734603
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321777B2

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