Triethylamine → HCID 86715778, compound

HRID 920180Notes

Reaction equation

HRID 920180 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([CH3:22])[CH2:16][S:15](=[O:18])(=[O:17])[C:14]([CH3:20])([CH3:19])[C:13]([NH2:21])=[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([CH3:22])[CH2:16][S:15](=[O:17])(=[O:18])[C:14]([CH3:19])([CH3:20])[C:13]([NH2:21])=[N:12]2)[CH:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 66562151HCID 66562151, compound

Product 1

HCID 86715778HCID 86715778, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-5-(2-fluoro-5-nitro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (950 mg, 2.88 mmol, Eq: 1.00) in ethanol (50 ml) was added at 23° C. under inert atmosphere triethylamine (292 mg, 402 μl, 2.88 mmol, Eq: 1.00) and after inertisation Pd/C 10% (307 mg, 288 μmol, Eq: 0.1). The suspension was set under hydrogen (balloon) and stirred at 23° C. for 1 hour. The catalyst was filtered off, washed three times with ethanol and a mixture of dichloromethane and methanol and evaporated the combined filtrate to give the crude and nearly pure (R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (760 mg, 2.54 mmol, 88.0% yield) as an off-white solid. MS (ISP): m/z=300.3 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed three times with ethanol
  3. additiona mixture of dichloromethane and methanol
  4. customevaporated the combined filtrate

Sources & evidence

ORD record
ord-a353894da846436b9683eb588cf4061d
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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