Trifluoroacetic acid → Methyl 8-amino-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate

HRID 595117Notes

Reaction equation

HRID 595117 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[CH2:20][CH2:19][C:18]=2[C:17]=1[C:29]([O:31][CH3:32])=[O:30])=O)(C)(C)C.C(OC(NC1C=CC2C3=CC=NN3CCC=2C=1C(OC)=O)=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[CH2:20][CH2:19][C:18]=2[C:17]=1[C:29]([O:31][CH3:32])=[O:30]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 70984431Methyl 8-tert-butoxycarbonylamino-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate2×HCID 70984636Methyl 8-[bis-(tert-butoxycarbonyl)amino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate

Product 1

HCID 86712823Methyl 8-amino-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a mixture of methyl 8-[bis-(tert-butoxycarbonyl)amino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate and methyl 8-tert-butoxycarbonylamino-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 23, 0.114 g) in DCM (2 mL) and the resultant mixture was stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate solution was added and the mixture was stirred for 15 minutes, then extracted with DCM, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 8-amino-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate (0.060 g) as a gum.

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-796da5ac38b9448cb0fc7528b7060789
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

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