Sodium Methoxide → 1-(2-{4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one

HRID 1644428Notes

Reaction equation

HRID 1644428 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:32])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20][CH2:21][C:22]3[N:27]=[CH:26][C:25]4[O:28][CH2:29][CH2:30][O:31][C:24]=4[CH:23]=3)[CH2:16][CH2:15]2)=[CH:4][CH:3]=1.[CH3:33][O-:34].[Na+]>CO>[O:31]1[C:24]2[CH:23]=[C:22]([CH2:21][NH:20][CH:17]3[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:9]4[C:10]5[C:5](=[CH:4][CH:3]=[C:2]([O:34][CH3:33])[N:11]=5)[CH:6]=[CH:7][C:8]4=[O:32])[CH2:15][CH2:16]3)[N:27]=[CH:26][C:25]=2[O:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 159824067-Chloro-1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 159824071-(2-{4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-7-methoxy-1,8-naphthyridin-2(1H)-oneYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-chloro-1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,8-naphthyridin-2(1H)-one (Example 67) (95 mg, 0.21 mmol) in methanol (5 mL) was treated with a solution of sodium methoxide (0.5 M, 1 mL, 0.5 mmol). The reaction mixture was sealed in a tube and heated at 150 C for 1 hour using microwave irradiation. The reaction mixture was concentrated at reduced pressure, partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (3×10 mL) and chloroform/methanol (4:1) (3×15 mL). The combined organic extracts were dried over sodium sulfate and concentrated at reduced pressure. Chromatography on silica gel using methanol in dichloromethane (0-50%) gave the product as a colorless solid (29 mg, 31%)

Workup

  1. customThe reaction mixture was sealed in a tube
  2. temperatureheated at 150 C for 1 hour
  3. custommicrowave irradiation
  4. concentrationThe reaction mixture was concentrated at reduced pressure
  5. custompartitioned between ethyl acetate and water
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL) and chloroform/methanol (4:1) (3×15 mL)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-15559da19c934becbf779da627db82ef
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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