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

HRID 595104Notes

Reaction equation

HRID 595104 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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%

Sources & evidence

ORD record
ord-40a0fc722c664f0d9dd2d29d8d7020ea
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

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