HCID 22725102, compound → HCID 22725100, compound

HRID 2086584Notes

Reaction equation

HRID 2086584 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]([C:18]1[C:23](Br)=[CH:22][N:21]=[CH:20][N:19]=1)([OH:17])[CH2:13]2>CO.CCOC(C)=O.N.CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1)([OH:17])[CH2:13]2

Participants

5

Reactant 1

HCID 22725102HCID 22725102, compound

Product 1

HCID 22725100HCID 22725100, compound

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 21584119Ethylacetate methanolSolventHCID 21705897Ammonia methanolSolvent

Procedure

Hydrogenate the product of Step 1 (22 mg) in CH3OH-EtOAc (1:1, 10 ml) and NH3/CH3OH (7N, 1 ml) in the presence of Lindlar catalyst at 1 atm for 2 h, filter and concentrate to produce the title compound. 1H NMR (CDCl3) δ9.15 (s, 1H), 8.70 (d, 1H), 8.00 (m, 2H), 7.80 (d, 1H), 7.25 (m, 4H), 7.19 (t, 2H), 5.61 (s, 1H), 3.15 (br s, 2H), 2.50 (dd, 2H), 2.25 (m, 4H), 1.65 (d, 2H).

Workup

  1. filtrationfilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-22ce3b385aa843e280846c10e07b3c24
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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