Formamide → HCID 18770879, compound

HRID 1352731Notes

Reaction equation

HRID 1352731 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[N:7]=1)C.C([NH2:26])=O.CO[Na]>CN(C=O)C.CO.C(O)(C)C>[CH3:22][N:19]1[CH2:20][CH2:21][N:16]([C:8]2[N:7]=[C:6]([CH2:5][C:4]([NH2:26])=[O:3])[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:17][CH2:18]1

Participants

7

Reactant 3

HCID 713FormamideHCID 68474051HCID 68474051, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 18770879HCID 18770879, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [3-(4-Methyl-piperazin-1-yl)-isoquinolin-1-yl]-acetic acid ethyl ester (1.7 g, 5.4 mmol) in DMF, formamide (0.72 ml, 18.1 mmol) is added under argon. After heating up to 100° C. 5.4N MeONa in methanol (1 ml) is added in 10 portions (0.1 ml each) over a period of 45 minutes. After 60 minutes at 100° C. the reaction is cooled to RT and diluted with isopropanol (100 ml). The solvents are removed under reduced pressure, the residue is dissolved in ethyl acetate and extracted with aqueous sodium bicarbonate solution (5%). The organic phase is dried (Na2SO4) and concentrated. The resulting crude is purified on silica gel using methylene chloride/methanol (90/10→80/20) as eluent obtaining the product as a white solid.

Workup

  1. temperatureAfter 60 minutes at 100° C. the reaction is cooled to RT
  2. customThe solvents are removed under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. extractionextracted with aqueous sodium bicarbonate solution (5%)
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting crude is purified on silica gel

Sources & evidence

ORD record
ord-ba2fedaa08fd44e1882dc86a2f8401a4
Source dataset
uspto-grants-2007_05
Patent number
US07220774B2

Reaction notes

Loading…