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

HRID 9145

反応式

HRID 9145 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒2 回HCID 887Methanol溶媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1d4c968dd1784c18a9903db176fc40d0
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

関連ノート

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