Cumylamine → 3-(2-Nitro-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide

HRID 1642335ノート

反応式

HRID 1642335 の反応式
NC1C=CC=CC=1[C:4]([NH:6][C:7]1[NH:11][N:10]=[C:9]2[CH:12]=[C:13]([C:15](O)=[O:16])[O:14][C:8]=12)=[O:5].C(N(C(C)C)CC)(C)C.[C:31]([NH2:40])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:33])[CH3:32].F[B-](F)(F)F.[N:46]1([O:55]C(N(C)C)=[N+](C)C)[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2N=N1.C(=O)(O)[O-:64].[Na+]>CN(C)C=O>[CH3:32][C:31]([NH:40][C:15]([C:13]1[O:14][C:8]2[C:7]([NH:6][C:4](=[O:5])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[N+:46]([O-:55])=[O:64])=[N:11][NH:10][C:9]=2[CH:12]=1)=[O:16])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33]

参加物

7

反応物 5

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178507499HCID 178507499、化合物

生成物 1

HCID 578786433-(2-Nitro-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide収率 24.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(2-Amino-benzoylamino)-furo[3,2-c]pyrazole-5-carboxylic acid (11.6 g, 0.03668 mol) was dissolved in anhydrous dimethyl formamide (DMF, 70 mL). Diisopropylethylamine (DIEA, 31.4 mL, 0.1834 mol), cumylamine (7.43 mL, 0.055 mol) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 15.31 g, 0.0476 mol) were added respectively added. The solution was stirred at room temperature overnight. Then it was poured in a saturated solution of sodium bicarbonate (700 mL) and extracted with dichloromethane (2×250 ml). The organic layer was washed with water and dried over Na2SO4. The solution was then evaporated to dryness, taken up with toluene and evaporated to dryness, taken up with ethyl ether and filtered off. The solid was then purified by flash column chromatography on silica gel eluting with dichloromethane-methanol 46/4. The title compound was so obtained (3.87 g, 24.4% yield).

後処理

  1. additionadded
  2. extractionextracted with dichloromethane (2×250 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solution was then evaporated to dryness
  6. customevaporated to dryness
  7. filtrationfiltered off
  8. customThe solid was then purified by flash column chromatography on silica gel eluting with dichloromethane-methanol 46/4

出典と根拠

ORDレコード
ord-626cf8f41fc6466cab3729b2fef5caef
出典データセット
uspto-grants-2012_02
特許番号
US08119641B2

反応ノート

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