HCID 57431646, compound → HCID 59161195, compound

HRID 545508Notes

Reaction equation

HRID 545508 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]([N+:23]([O-])=O)[CH:18]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:7][C:6]2=1)#[N:2]>[Pt].CO>[NH2:23][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:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:7][C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[C:3]([C:1]#[N:2])[CH:4]=2

Participants

4

Reactant 1

HCID 57431646HCID 57431646, compound

Product 1

HCID 59161195HCID 59161195, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Add sulfided platinum (5 wt % on carbon) (120 mg) to a solution of N-[6-cyano-9-(3-nitro-benzyl)2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 88) (470 mg, 1.1 mmol) and methanol (50 mL). Purge and fill the reaction vessel with nitrogen (3×), then with hydrogen (3×, 55 psi). Seal the reaction vessel at about 55 psi, and stir the mixture at room temperature overnight. Filter the reaction mixture through a Celite® pad, and wash the filter cake with methanol. Concentrate under reduced pressure and purify the crude residue by flash chromatography (2.5% methanol/methylene chloride) to give the title compound. LCMS (Method D): m/z 387.1 (M+1, APCI); 1H NMR (DMSO-d6): δ 7.97 (d, 1H), 7.88 (d, 1H), 7.57 (d, 1H), 7.42 (dd, 1H), 6.94 (t, 1H), 6.24 (d, 1H), 6.20 (m, 1H), 5.26 (s, 2H), 5.07 (s, 2H), 4.03-4.06 (m, 1H), 3.01 (dd, 1H), 2.72-2.86 (m, 2H), 2.55 (dd, 1H), 2.38-2.46 (m, 1H), 1.98-2.02 (m, 2H), 1.79-1.87 (m, 1H), 1.04 (d, 3H), 1.02 (d, 3H).

Workup

  1. customPurge
  2. customSeal the reaction vessel at about 55 psi
  3. filtrationFilter the reaction mixture through a Celite® pad
  4. washwash the filter cake with methanol
  5. concentrationConcentrate under reduced pressure
  6. custompurify the crude residue by flash chromatography (2.5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-ac33bc4a10114e18aedbdc222b1eb4a0
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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