HCID 10340909, compound → HCID 10475768, compound

HRID 2293920Notes

Reaction equation

HRID 2293920 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1.[CH3:21][O-:22].[Na+]>CO>[I:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:12][C:4]1[N:3]=[C:2]([O:22][CH3:21])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:11]

Participants

4

Reactant 2

HCID 10340909HCID 10340909, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10475768HCID 10475768, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of compound 6 (21 mg, 0.052 mmol) and sodium methoxide in methanol (1.5 mg of Na) was heated for 14 h at 85° C. After evaporation of the solvent, the residue was triturated with methanol-water to give compound 15 (19 mg, 86.0%). 1H NMR (DMSO-d6) δ 3.64 (s, 3 H, 9-CH3), 3.81 (s, 3 H, OCH3), 4.59 (br s, 2 H, CH2), 7.11 (t, J=7.6 Hz, 1 H, H-16), 7.37 (d, J=7.6 Hz, 1 H, H-17), 7.59 (d, J=7.6 Hz, 1 H, H-15), 7.74 (s, 1 H, H-13), 7.92 (s, 1 H, H-8), 8.37 (br s, 1 H, exchangeable with D2O, NH).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was triturated with methanol-water

Sources & evidence

ORD record
ord-d4590d4e043042aa951465e257e4facd
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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