Dimethylformamide → HCID 67173491, compound

HRID 872481Notes

Reaction equation

HRID 872481 reaction equation
[N+]([C:4]1[CH:5]=[CH:6][C:7]([C:14]2[NH:18][N:17]=[CH:16][CH:15]=2)=[C:8]2[C:13]=1[CH:12]=[N:11][CH:10]=[CH:9]2)([O-])=O.CN(C=O)C.CS(O[CH2:29][CH2:30][NH:31]C(OC(C)(C)C)=O)(=O)=O.Cl.CCO>C(OCC)C.O>[CH:12]1[C:13]2[C:8](=[C:7]([C:14]3[CH:15]=[CH:16][N:17]([CH2:29][CH2:30][NH2:31])[N:18]=3)[CH:6]=[CH:5][CH:4]=2)[CH:9]=[CH:10][N:11]=1

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 21887872Ethanol hydrochlorideHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamateHCID 67171393HCID 67171393, compound

Product 1

HCID 67173491HCID 67173491, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 0.50 g of 8-nitro-5-(1H-pyrazol-5-yl)isoquinoline was added 5 ml of dry DMF and the mixture was stirred at RT for 30 min. To this was added 0.65 g of 2-(tert-butoxycarbonylamino)ethyl methanesulfonate diluted to 1.5 ml of dry DMF and the mixture was microwaved for 30 min at 160° C. After pouring the mixture to water, it was extracted with EtOAc. Combined organic phases were washed with water and brine, dried with Na2SO4 and evaporated. Crude product was purified by CombiFlash (5% MeOH in DCM). Product fractions were combined and evaporated to give 0.59 g of Boc-protected product. For Boc deprotection 8 ml of 10% HCl/EtOH solution was added to the evaporation residue, stirred at RT until disappearance of starting material by TLC. 3 ml of diethylether was added to the mixture and the precipitate was filtered, washed with diethylether and dried to give 0.30 g of the product as HCl-salt. 1H-NMR (400 MHz; d6-DMSO): δ 1.57 (br s, 2H), 3.04 (t, 2H), 4.25 (t, 2H), 6.90 (d, 1H), 8.00 (d, 1H), 8.17 (d, 1H), 8.47 (d, 1H), 8.75 (d, 1H), 8.91 (d, 1H), 9.83 (s, 1H).

Workup

  1. customthe mixture was microwaved for 30 min at 160° C
  2. extractionwas extracted with EtOAc
  3. washCombined organic phases were washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customCrude product was purified by CombiFlash (5% MeOH in DCM)
  7. customevaporated
  8. customto give 0.59 g of Boc-protected product
  9. stirringstirred at RT until disappearance of starting material by TLC
  10. filtrationthe precipitate was filtered
  11. washwashed with diethylether
  12. customdried

Sources & evidence

ORD record
ord-9eb4f3a1083a4968b682b160500cf808
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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