Lithium Hydroxide → HCID 89832349, compound

HRID 338157Notes

Reaction equation

HRID 338157 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[CH2:16][N:15]([C:17]3[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=3)[CH2:14][CH:13]1[CH2:12][S:11][C:10]([NH:24]C(=O)C1C=CC=CC=1)=[N:9]2.[OH-].[Li+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[CH2:16][N:15]([C:17]3[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=3)[CH2:14][CH:13]1[CH2:12][S:11][C:10]([NH2:24])=[N:9]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89832319HCID 89832319, compound

Product 1

HCID 89832349HCID 89832349, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic N-[7a-(2-fluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (560 mg, 1.24 mmol), methanol (12 ml), and lithium hydroxide (208 mg, 4.95 mmol) is heated to 50° C. for 18 hours under an atmosphere of nitrogen. The methanol is removed to near dryness with a stream of nitrogen. To the reaction is added ethyl acetate (7.5 ml), and water (2.5 ml). The mixture is passed through 10 g diatomaceous earth and the solvent removed under reduced pressure. The filtrate is passed through a 8 g XL-C solid phase extraction column (SPE), the basic methanol wash collected, and the solvent removed under reduced pressure to provide the crude title compound (370 mg, 86%). ES/MS (m/e): 348 (M+H).

Workup

  1. customThe methanol is removed
  2. additionTo the reaction is added ethyl acetate (7.5 ml), and water (2.5 ml)
  3. customthe solvent removed under reduced pressure
  4. extractionThe filtrate is passed through a 8 g XL-C solid phase extraction column (SPE)
  5. washthe basic methanol wash
  6. customcollected
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0576bed166ba44fa851eff32d84d0445
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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