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

HRID 920179Notes

Reaction equation

HRID 920179 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]1([CH3:20])[CH2:16][S:15](=[O:18])(=[O:17])[CH2:14][C:13]([NH2:19])=[N:12]1.C(N(CC)CC)C>C(O)C.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]2([CH3:20])[CH2:16][S:15](=[O:17])(=[O:18])[CH2:14][C:13]([NH2:19])=[N:12]2)[CH:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 118073003(R)-5-(2-fluoro-5-nitro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

Product 1

HCID 90067101(R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamineYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)-5-(2-fluoro-5-nitro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (584 mg, 1.94 mmol, Eq: 1.00) in ethanol (45 ml), triethylamine (196 mg, 270 μl, 1.94 mmol, Eq: 1.00) and Pd/C (206 mg, 194 μmol, Eq: 0.1) was hydrogenated at room temperature for 1 hour. Filtered off the catalyst, washed with ethanol, evaporated the filtrate and dried in HV to give the (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (460 mg, 1.7 mmol, 87.5% yield) as a an off-white foam. MS (ISP): m/z=272.4 [M+H]+.

Workup

  1. filtrationFiltered off the catalyst
  2. washwashed with ethanol
  3. customevaporated the filtrate
  4. customdried in HV

Sources & evidence

ORD record
ord-ede3ac0b985a4fc8bc55189a5a33386b
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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