(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine → (R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

HRID 920169Notes

Reaction equation

HRID 920169 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[CH2:13][S:12](=[O:15])(=[O:14])[CH2:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1>CO.N.[Pd]>[F:18][C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=1[C@:8]1([CH3:17])[CH2:13][S:12](=[O:14])(=[O:15])[CH2:11][C:10]([NH2:16])=[N:9]1

Participants

5

Reactant 1

HCID 90067098(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

Product 1

HCID 90067085(R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamineYield 86.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent2×

Procedure

To a solution of (R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (750 mg, 2.24 mmol, Eq: 1.00) in methanol (150 ml) and 7 M ammonia in methanol (959 μl, 6.71 mmol, Eq: 3) at room temperature added Pd/C (238 mg, 224 mmol, Eq: 0.1) and the mixture was hydrogenated at room temperature for 2 hours. Extracted with dichloromethane and some 25% ammonium hydroxide solution. Dried the organic layer over Na2SO4, filtered off and evaporated totally, dried in HV to give the (R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (497 mg, 1.94 mmol, 86.7% yield) as a white foam. MS (ISP): m/z=257.1 [M+H]+.

Workup

  1. extractionExtracted with dichloromethane
  2. dry with materialDried the organic layer over Na2SO4
  3. filtrationfiltered off
  4. customevaporated totally
  5. customdried in HV

Sources & evidence

ORD record
ord-eba616dfc0b34ece9512ba3015c3bb7c
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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