Sodium Methoxide → HCID 20816860, compound

HRID 897369Notes

Reaction equation

HRID 897369 reaction equation
[O:1]=[S:2]1(=[O:43])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:31])(=[O:30])=[O:29])=[O:19])[C:15](C2C=C(C)C=CC=2S([O-])(=O)=O)=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.C[O-:45].[Na+]>CO.O>[O:1]=[S:2]1(=[O:43])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:31])(=[O:30])=[O:29])=[O:19])[C:15]([OH:45])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 86587467HCID 86587467, compound

Product 1

HCID 20816860HCID 20816860, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

5-(1,1-dioxido-1,2-thiazinan-2-yl)-7-({[2-(methylsulfonyl)benzyl]amino}carbonyl)-1,6-naphthyridin-8-yl-4-methylbenzenesulfonate (220 mg, 0.34 mmol) was dissolved in methanol (10 mL) and NaOMe (55 mg, 1.02 mmol) was added. The reaction was stirred overnight at room temperature. The crude reaction was diluted with water (10 mL) and extracted with CH2Cl2 (2×10 mL). The organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford a yellow oily solid. The material was suspended in methanol and a yellow precipitate fell out of solution. Washing with fresh methanol (2×10 mL) gave the desired product as an off-white solid.

Workup

  1. customThe crude reaction
  2. extractionextracted with CH2Cl2 (2×10 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow oily solid
  7. washWashing with fresh methanol (2×10 mL)

Sources & evidence

ORD record
ord-30ec053c938a4373ae6e42e46afa82e6
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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