Ethylamine → HCID 131729373, compound

HRID 420294Notes

Reaction equation

HRID 420294 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:29](=[O:32])[CH2:30]Cl)=[C:23]([CH2:33][CH3:34])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11][C:10]1=[O:35])([CH3:4])([CH3:3])[CH3:2].[CH2:39]([NH2:41])[CH3:40].CCOC(C)=O.CO>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:29](=[O:32])[CH2:30][NH:41][CH2:39][CH3:40])=[C:23]([CH2:33][CH3:34])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11][C:10]1=[O:35])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 21584119Ethylacetate methanolHCID 131729372HCID 131729372, compound

Product 1

HCID 131729373HCID 131729373, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-{4-[(3aR,7S,7aS)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-ethyl-6-fluoro-phenyl}-2-chloro-acetamide 0.087 g, 0.15 mmol) in DMF (2 mL) was added a 4M solution of ethylamine in DMF (0.1 mL, 0.4 mmol) and the reaction mixture was kept for 2 days at 25° C. After evaporation, the product was dissolved in water and extracted with EtOAc. Combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to provide a yellow foam: TLC (EtOAc-MeOH 9:1) Rf=0.25; UPLC RtD=1.443 min; ESIMS [M+NH4]+=574.

Workup

  1. customAfter evaporation
  2. dissolutionthe product was dissolved in water
  3. extractionextracted with EtOAc
  4. washCombined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto provide a yellow foam
  9. customUPLC RtD=1.443 min

Sources & evidence

ORD record
ord-62bc2d4e26424e1c8693023ab56f39bc
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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