Ammonia → HCID 22725079, compound

HRID 2086587Notes

Reaction equation

HRID 2086587 reaction equation
[N:1]([CH2:4][C:5]1[N:10]=[C:9]([C:11]2([OH:34])[CH2:17][CH:16]3[N:18]([CH:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:26])[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH:8]=[CH:7][CH:6]=1)=[N+]=[N-].N>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCOC(C)=O.CO>[NH2:1][CH2:4][C:5]1[N:10]=[C:9]([C:11]2([OH:34])[CH2:17][CH:16]3[N:18]([CH:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:26])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 22725084HCID 22725084, compound

Product 1

HCID 22725079HCID 22725079, compound

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add Lindlar catalyst (44 mg) to a suspension of the product from Step 5 (279 mg) in a mixture of EtOAc and CH3OH in the presence of 7N NH3 in CH3OH (1 ml). Hydrogenate the mixture at 1 atm for 1.5 h, filter through celite, wash with NH3/CH3OH (3.5 N) and concentrate to give the desired compound.

Workup

  1. filtrationfilter through celite
  2. washwash with NH3/CH3OH (3.5 N)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-d30703a3fcc14e6eb86433155ffeec4d
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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