Dimethylformamide → 1-(5-(Benzyloxy)-7-cyanobenzo[d]thiazol-2-yl)-3-ethylurea

HRID 712268노트

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HRID 712268 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Zn+2].C([O-])(=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:25]#[N:26])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 2

HCID 6228DimethylformamideHCID 578136291-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

생성물 1

HCID 866639801-(5-(Benzyloxy)-7-cyanobenzo[d]thiazol-2-yl)-3-ethylurea수율 100%

시약·촉매·용매 6

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11192Zinc Acetate촉매HCID 23994Zinc촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

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온도
100 °C

실험 절차

1-(5-(benzyloxy)-7-bromobenzo[d]thiazol-2-yl)-3-ethylurea (5.00 g, 12.29 mmol), zinc cyanide (1.58 g, 13.49 mmol), 1,1′-bis(diphenylphosphino)ferrocene (20 mg, 0.033 mmol), zinc acetate (90 mg, 0.50 mmol) and zinc dust (33.3 mg, 0.50 mmol) were stirred in a reaction tube in degassed DMF (60 ml) and water (600 ul). Tris(dibenzylideneacetone)dipalladium(0) (113.2 mg, 0.133 mmol) was added and the reaction purged with N2, sealed and heated to 100° C. for 18 h with stirring. LCMS indicated clean conversion to the desired material. The solvents were removed under reduced pressure, the resulting residue triturated with water, the solid collected by filtration and dried in a vacuum oven to afford the desired material as a pale white solid 4.4 g (100%). This material was used directly in the next step with no further purification.

후처리

  1. customthe reaction purged with N2
  2. customsealed
  3. customThe solvents were removed under reduced pressure
  4. customthe resulting residue triturated with water
  5. filtrationthe solid collected by filtration
  6. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-c254583292a64119901cd80fe1599e1c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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