Methanesulfonyl chloride → Methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate

HRID 595105Notes

Reaction equation

HRID 595105 reaction equation
CS(Cl)(=O)=O.[C:6]([O:10][C:11]([N:13]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:14]1[CH:23]=[CH:22][C:21]2[C:20]3=[CH:24][CH:25]=[N:26][N:19]3[CH2:18][CH:17](O)[C:16]=2[C:15]=1[C:28]([O:30][CH3:31])=[O:29])=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(N(CC)CC)C.C(Cl)Cl>[C:35]([O:34][C:32]([N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[C:14]1[CH:23]=[CH:22][C:21]2[C:20]3=[CH:24][CH:25]=[N:26][N:19]3[CH:18]=[CH:17][C:16]=2[C:15]=1[C:28]([O:30][CH3:31])=[O:29])=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71005652Methyl 8-[bis-(tert-butoxycarbonyl)amino]-6-hydroxy-5,6-dihydro-pyrazolo[5,1-a]isoquinoline-7-carboxylate2×

Product 1

HCID 70984535Methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylateYield 100.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methanesulfonyl chloride (0.5 mL) was added to a solution of methyl 8-[bis-(tert-butoxycarbonyl)amino]-6-hydroxy-5,6-dihydro-pyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 8, 0.290 g) in triethylamine (0.7 mL) and DCM (10 mL) and the reaction mixture was stirred at room temperature for 30 minutes. The resultant mixture was washed with 1M aqueous hydrochloric acid and the organic layer was separated, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate (0.280 g) as a gum.

Workup

  1. washThe resultant mixture was washed with 1M aqueous hydrochloric acid
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c7209ccaa39648919564c25d4ec7b1fc
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

Loading…