Boric Acid → 1-(6-(3-Aminophenyl)-2-benzothiazolyl)-3-ethylurea

HRID 9145

Reaction equation

HRID 9145 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1.[NH2:17][C:18]1[CH:19]=[C:20](OB(O)O)[CH:21]=[CH:22][CH:23]=1.C(=O)(O)[O-].[Na+].B(O)(O)O>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.O>[NH2:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:16]=[CH:15][C:5]3[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=3[CH:3]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7628Boric AcidHCID 516892Sodium BicarbonateHCID 218958363-Aminophenylboric acidHCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855751-(6-(3-Aminophenyl)-2-benzothiazolyl)-3-ethylureaYield 23.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 887MethanolSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea (0.300 g, 1.00 mmol), 3-aminophenyl boric acid (0.237 g, 1.50 mmol, 1.5 eq), and sodium bicarbonate (0.210 g, 2.50 mmol, 2.5 eq) in 8 mL of mixed solvent DMF/water (5/1) was purged with nitrogen gas. To the mixture, the catalyst Pd(PPh3)4 (0.058 g, 0.05 mmol, 0.05 eq) was added. It was purged with nitrogen gas again, and was heated at about 100° C. in a sealed tube for about 48 hours. More Pd(PPh3)4 (0.025 g, 0.02 mmol, 0.02 eq) and more boric acid (0.080 g, 0.50 mmol, 0.50 eq) were added after the first 24 hours. The mixture was taken up in MeOH, concentrated, dissolved in methylene chloride, washed with sodium bicarbonate solution, dried (MgSO4), evaporated, and purified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50) to give the desired compound 0.073 g (23%). LC/MS 313.2 (M+1); LC retention time 2.11 min.

Workup

  1. customwas purged with nitrogen gas
  2. customIt was purged with nitrogen gas again
  3. concentrationconcentrated
  4. dissolutiondissolved in methylene chloride
  5. washwashed with sodium bicarbonate solution
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. custompurified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50)

Sources & evidence

ORD record
ord-1d4c968dd1784c18a9903db176fc40d0
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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