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

HRID 712268Notes

Reaction equation

HRID 712268 reaction equation
[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

Participants

9

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 6

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11192Zinc AcetateCatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c254583292a64119901cd80fe1599e1c
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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