Sodium Hydroxide → HCID 67416092, compound

HRID 2193014Notes

Reaction equation

HRID 2193014 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:27]=[N:26][CH:25]=[CH:24][C:5]=1[C:6]([CH2:12][S:13]([N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:14])=[N:7]2.[OH-:28].[Na+]>C(O)(=O)C.O>[CH3:23][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:13]([CH2:12][C:6]1[C:5]2[CH:24]=[CH:25][N:26]=[CH:27][C:4]=2[C:3]2[C:2](=[O:28])[NH:11][CH:10]=[CH:9][C:8]=2[N:7]=1)(=[O:14])=[O:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59375562HCID 59375562, compound

Product 1

HCID 67416092HCID 67416092, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(1-chloropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-methyl-N-phenylmethanesulfonamide (45 mg, 0.113 mmol) in acetic acid (2790 μl) and water (1196 μl) was heated to 100° C. and stirred for 2 h. After cooling to room temperature, the reaction mixture was added to aqueous sodium hydroxide (1M). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford N-methyl-1-(1-oxo-1,2-dihydropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-phenylmethanesulfonamide as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 12.17 (s, 1H), 11.19 (s, 1H), 8.87 (d, 1H), 8.30 (d, 1H), 7.71 (t, 1H), 7.48 (d, 2H), 7.38 (t, 2H), 7.29 (t, 1H), 6.95 (d, 1H), 5.36 (s, 2H), 3.22 (s, 3H). LRMS (APCI) calc'd for (C14H14N3O) [M+H]+, 381.1; found 381.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  6. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-35eeaca40656457baafc6b1db5eaae63
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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