HCID 67199568, compound → HCID 67202012, compound

HRID 547538Notes

Reaction equation

HRID 547538 reaction equation
[Cl-:1].[C:2]([NH:5][C:6]1[CH:25]=[CH:24][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=3)[NH+:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])[CH3:3]>CO.[Pd]>[Cl-:1].[C:2]([NH:5][C:6]1[CH:25]=[CH:24][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=3)[NH+:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 1

HCID 67199568HCID 67199568, compound

Product 1

HCID 67202012HCID 67202012, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of (A3 (1.75 g, 4.88 mmol) in MeOH (10 mL) was added 10% Pd/C (0.1 g) and hydrogenated (under 40 psi). for 2 h. The reaction mixture was filtered and washed with more MeOH. The filtrated was concentrated to half the volume, diluted with EtOAc and the rest of the MeOH was evaporated. The Resulting precipitate was filtered washed with more EtOAc and dried to give essentially pure (A4) (1.255 g 78%); mp (MeOH/EtOAc)>280° C.; 1H NMR [(CD3)2SO] δ13.95 (br, 1 H, N+H), 10.14 (s, 1 H, NH), 10.01 (s, 1H, NH), 8.10 (d, J=6.7 Hz, 1 H, ArH), 7.74 (d, J=8.9 Hz, 3 H, ArH), 7.43 (d, J=2.2 Hz, 1 H, ArH), 7.38-7.32 (m, 3 H, ArH), 6.61 (d, J=6.7 Hz, 1 H, ArH), 5.94 (s, 2 H, NH2), 2.08 (s, 3 H, COCH3); APCI+ve 293.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with more MeOH
  3. concentrationThe filtrated was concentrated to half the volume
  4. additiondiluted with EtOAc
  5. customthe rest of the MeOH was evaporated
  6. filtrationThe Resulting precipitate was filtered
  7. washwashed with more EtOAc
  8. customdried

Sources & evidence

ORD record
ord-0f699cec04a246bead317f3870c02fb5
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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