Trifluoroacetic acid → Methyl 8-aminopyrazolo[5,1-a]isoquinoline-7-carboxylate

HRID 595104ノート

反応式

HRID 595104 の反応式
C(O)(C(F)(F)F)=O.C(OC([N:15](C(OC(C)(C)C)=O)[C:16]1[CH:25]=[CH:24][C:23]2[C:22]3=[CH:26][CH:27]=[N:28][N:21]3[CH:20]=[CH:19][C:18]=2[C:17]=1[C:29]([O:31][CH3:32])=[O:30])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:22]3=[CH:26][CH:27]=[N:28][N:21]3[CH:20]=[CH:19][C:18]=2[C:17]=1[C:29]([O:31][CH3:32])=[O:30]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 70984535Methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate2 回

生成物 1

HCID 86712816Methyl 8-aminopyrazolo[5,1-a]isoquinoline-7-carboxylate収率 91.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TFA (3 mL) was added to a solution of methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 7, 0.280 g) in DCM (3 mL) and the reaction mixture was stirred at room temperature for 2 hours. The mixture was stirred with saturated aqueous sodium bicarbonate solution for 30 minutes and then the organic layer was separated, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give methyl 8-aminopyrazolo[5,1-a]isoquinoline-7-carboxylate (0.140 g) as a glass.

後処理

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

出典と根拠

ORDレコード
ord-40a0fc722c664f0d9dd2d29d8d7020ea
出典データセット
uspto-grants-2016_01
特許番号
US09242997B2

反応ノート

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