Pyridine → HCID 86612975, compound

HRID 1366744Notes

Reaction equation

HRID 1366744 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:7][CH:6]=[CH:5]2.C(N(CC)CC)C.N1C=CC=CC=1.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[S:37]>O1CCCC1.CCCCCCC.C(OCC)(=O)C>[C:13]([NH:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][C:36](=[S:37])[N:35]([CH3:39])[CH3:34])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 136378998HCID 136378998, compound

Product 1

HCID 86612975HCID 86612975, compoundYield 52.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-(6-hydroxyisoquinolin-1-yl)benzamide (100 mg, 0.379 mmol), triethylamine (105 mL, 0.758 mmol) and pyridine (306 mL, 3.79 mmol) in anhydrous tetrahydrofuran (2 ml) was added N,N-dimethylthiocarbamoyl chloride (70 mg, 0.568 mmol) at 0° C., under nitrogen. The mixture was heated to 65° C. and stirred for 48 h. The organics were removed under reduced pressure and excess pyridine was removed by azeotroping with toluene (x 2). Saturated aqueous NaHCO3 was added and the mixture was extracted with dichloromethane (x 2), dried (magnesium sulphate) and concentrated in vacuo to give a residue. Flash chromatography of the residue (eluent: 5-50% ethyl acetate in heptane) gave dimethylthiocarbamic acid O-(1-benzoylaminoisoquinolin-6-yl)ester (70 mg), EIMS: m/z=352.7 [M+H]+.

Workup

  1. customThe organics were removed under reduced pressure and excess pyridine
  2. customwas removed
  3. customby azeotroping with toluene (x 2)
  4. additionSaturated aqueous NaHCO3 was added
  5. extractionthe mixture was extracted with dichloromethane (x 2)
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-a02583e48f4040f088523700944135ba
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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