Triethylamine → HCID 89419817, compound

HRID 920181Notes

Reaction equation

HRID 920181 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([CH3:24])[N:20]=[C:19]([NH2:21])[C:14]2([CH2:18][CH2:17][CH2:16][CH2:15]2)[S:13](=[O:23])(=[O:22])[CH2:12]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([CH3:24])[N:20]=[C:19]([NH2:21])[C:14]3([CH2:18][CH2:17][CH2:16][CH2:15]3)[S:13](=[O:22])(=[O:23])[CH2:12]2)[CH:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 89419819HCID 89419819, compound

Product 1

HCID 89419817HCID 89419817, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-8-(2-fluoro-5-nitro-phenyl)-8-methyl-6,6-dioxo-6λ6-thia-9-aza-spiro[4.5]dec-9-en-10-ylamine (210 mg, 591 μmol, Eq: 1.00) in ethanol (10 ml) was added at 23° C. under inert atmosphere triethylamine (59.8 mg, 82.4 μl, 591 μmol, Eq: 1.00) and after inertisation Pd/C 10% (62.9 mg, 59.1 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 evaporated to give the crude and nearly pure (R)-8-(5-amino-2-fluoro-phenyl)-8-methyl-6,6-dioxo-6λ6-thia-9-aza-spiro[4.5]dec-9-en-10-ylamine (182 mg, 559 μmol, 94.7% yield) as an off-white foam. MS (ISP): m/z=326.5 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed three times with ethanol
  3. customevaporated

Sources & evidence

ORD record
ord-3393ad4aae6d476c876897285cc5e3ef
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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