Diethyl Ether → HCID 66940223, compound

HRID 1910176Notes

Reaction equation

HRID 1910176 reaction equation
S(Cl)([Cl:4])(=O)=O.N1C=CN=C1NC(C1C2N=C(N[C:24]([C:26]3[N:27]=[CH:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][C:30]=4[O:36][CH3:37])=[O:25])NC=2C=CC=1)=O.CC[O:40][CH2:41]C>C(O)(=O)C>[CH3:41][O:40][C:24]([C:26]1[N:27]=[CH:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[C:31]([Cl:4])[C:30]=2[O:36][CH3:37])=[O:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 580265288-methoxy-isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide

Product 1

HCID 66940223HCID 66940223, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.083 mL (1 mmol) of sulfuryl chloride was added to a solution of 90 mg (0.41 mmol) of 8-methoxy-isoquinoline-3-carboxylic acid methyl ester (from Example 295) in 1 mL of acetic acid and stirred at room temperature overnight. Ether was added to the reaction mixture, and the precipitated solid was filtered, washed with ether, then partitioned between ethyl acetate (30 mL) and saturated NaHCO3 solution (30 mL) and extracted. The organic layer was dried over sodium sulfate, and evaporation of the solvent in vacuo gave 47.3 mg (46%) of 7-chloro-8-methoxy-isoquinoline-3-carboxylic acid methyl ester. LCMS: 252 (M+1)+. The ester was hydrolyzed according to the general procedure B to provide 40 mg (88%) of the 7-chloro-8-methoxy-isoquinoline-3-carboxylic acid. LCMS: 238 (M+1)+.

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with ether
  3. custompartitioned between ethyl acetate (30 mL) and saturated NaHCO3 solution (30 mL)
  4. extractionextracted
  5. dry with materialThe organic layer was dried over sodium sulfate, and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-1832a380e29a4be69e4ec28ba2e071e4
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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