Hydrochloric Acid → HCID 71738999, compound

HRID 1619061Notes

Reaction equation

HRID 1619061 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:16][C@@H:15]3[C@@:10]([C:26]4[S:30][N:29]=[CH:28][CH:27]=4)([N:11]=[C:12]([NH:17]C(=O)C4C=CC=CC=4)[S:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.[OH-].[Li+].Cl>CO.O>[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:16][C@@H:15]3[C@@:10]([C:26]4[S:30][N:29]=[CH:28][CH:27]=4)([N:11]=[C:12]([NH2:17])[S:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86762243HCID 86762243, compound

Product 1

HCID 71738999HCID 71738999, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

N-[(4aR,7aR)-6-(5-Fluoropyrimidin-2-yl)-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (5 g, 11.5 mmol) is added to lithium hydroxide (530 mg, 12.6 mmol) in methanol (50 mL) at 22° C. The reaction mixture is refluxed for 3 hours and then cooled to 22° C. Hydrogen chloride, 2 M in water (20.3 mL) is added and then solvent is evaporated. The solution is washed with MTBE (50 mL). The aqueous solution is treated with charcoal (500 mg) and stirred 30 minutes at 22° C. The mixture is filtered over diatomaceous earth and the pH of the filtrate is adjusted to pH=9 with sodium hydroxide (2M aqueous solution). A white solid precipitates and is collected. The solid is dried under vacuum to a constant weight to give the title compound (1 g, 30%). ES/MS (m/e): 337 (M+H).

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. customsolvent is evaporated
  3. washThe solution is washed with MTBE (50 mL)
  4. additionThe aqueous solution is treated with charcoal (500 mg)
  5. filtrationThe mixture is filtered over diatomaceous earth
  6. customA white solid precipitates
  7. customis collected
  8. customThe solid is dried under vacuum to a constant weight

Sources & evidence

ORD record
ord-f5ecb974e0d54daa805b9eff332579d0
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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