Triethylamine → HCID 89419882, compound

HRID 920182Notes

Reaction equation

HRID 920182 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([CH3:23])[N:19]=[C:18]([NH2:20])[C:14]2([CH2:17][CH2:16][CH2:15]2)[S:13](=[O:22])(=[O:21])[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([CH3:23])[N:19]=[C:18]([NH2:20])[C:14]3([CH2:17][CH2:16][CH2:15]3)[S:13](=[O:21])(=[O:22])[CH2:12]2)[CH:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 89419880HCID 89419880, compound

Product 1

HCID 89419882HCID 89419882, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-7-(2-fluoro-5-nitro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (470 mg, 1.38 mmol, Eq: 1.00) in ethanol (10 ml) was added at 23° C. under inert atmosphere triethylamine (139 mg, 192 μl, 1.38 mmol, 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 (R)-7-(5-amino-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (345 mg, 1.11 mmol, 80.5% yield) as a light brown solid. MS (ISP): m/z=312.5 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-01f9823823da44cabf5adeac17397b67
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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