Sodium Bicarbonate → HCID 57473506, compound

HRID 545504Notes

Reaction equation

HRID 545504 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:7][C:6]2=1)#[N:2].C(N)(=[S:32])C.C([O-])(O)=O.[Na+]>Cl.O1CCOCC1>[F:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:12]1[C:11]2[CH2:10][CH2:9][CH:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:7][C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[C:3]([C:1](=[S:32])[NH2:2])[CH:4]=2

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723949ThioacetamideHCID 57431643HCID 57431643, compound

Product 1

HCID 57473506HCID 57473506, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat N-(6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Example 51) (1.00 g, 2.57 mmol) with thioacetamide (0.386 g, 5.14 mmol) at reflux temperature in 4N HCl in dioxane (30 mL) for 4 h. Allow to cool, pour onto water and neutralize with NaHCO3. Collect 0.98 g (90%) of a precipitate. Purify a portion of the material by silica gel chromatography (25-80% EtOAc/hexanes gradient) to give a yellow solid. MS (ES): m/z 424 (M+1); HPLC: Rt=1.90 min, (95%).

Workup

  1. temperatureto cool
  2. additionpour onto water
  3. customCollect 0.98 g (90%) of a precipitate
  4. customPurify a portion of the material by silica gel chromatography (25-80% EtOAc/hexanes gradient)
  5. customto give a yellow solid

Sources & evidence

ORD record
ord-8b133fee3f844b569f773c30dbc9de0a
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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