Sodium Bicarbonate → HCID 59161227, compound

HRID 545530Notes

Reaction equation

HRID 545530 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([C:25]1[S:26]C=N[N:29]=1)[CH:11]=2.C(N)(=S)C.C([O-])(O)=O.[Na+]>Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([C:25](=[S:26])[NH2:29])[CH:11]=2

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723949ThioacetamideHCID 59161259HCID 59161259, compound

Product 1

HCID 59161227HCID 59161227, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat (R)-N-(6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Example 127) (4.00 g, 10.3 mmol) with thioacetamide (1.54 g, 20.5 mmol) at reflux in 4N HCl in dioxane (100 mL) for 16 h. Cool the reaction, pour onto water, and neutralize with NaHCO3. Extract with EtOAc and evaporate to 4.2 g of a red foam. Purify using silica gel chromatography, eluting with 25-100% EtOAc/hexanes gradient to give 2.6 g (60%) of a yellow solid. MS (ES): m/z 424 (M+1); HPLC: Rt=1.90 min (95%).

Workup

  1. temperatureCool
  2. customthe reaction
  3. additionpour onto water
  4. extractionExtract with EtOAc
  5. customevaporate to 4.2 g of a red foam
  6. customPurify
  7. washeluting with 25-100% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-451fdc23c51343819b31d7820d561afc
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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