Water → HCID 68539553, compound

HRID 1992279Notes

Reaction equation

HRID 1992279 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:16])[CH2:14][CH2:13][S:12][C:11]([NH2:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:16])[CH2:14][CH2:13][S:12][C:11]([NH:15][C:23](=[O:25])[CH3:24])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57948959HCID 57948959, compound

Product 1

HCID 68539553HCID 68539553, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-4-(3-bromo-4-fluorophenyl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-amine (550 mg, 1.8 mmoles, 1.0 equiv) in tetrahydrofuran (20 mL) is added pyridine (720 mg, 9.0 mmoles, 5 equiv) and acetic acid anhydride (220 mg, 2.2 mmoles, 1.2 equiv). After 10 minutes, the reaction is poured into water and the aqueous mixture is extracted with dichloromethane. The organic phase is separated and washed with 1N HCl and saturated aqueous NaCl, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (83% yield): MS (m/z) 345, 347 (M+1).

Workup

  1. extractionthe aqueous mixture is extracted with dichloromethane
  2. customThe organic phase is separated
  3. washwashed with 1N HCl and saturated aqueous NaCl
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a39bda73df8407db64cc8dfb7265d53
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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