2',4'-Dichloro-biphenyl-4-carboxylic acid → 2',4'-Dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzooxazol-5-yl}-amide
Reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]([CH3:16])[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:9]=2[N:10]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:26]1[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=1>>[ClH:18].[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]([CH3:16])[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([NH:15][C:32]([C:29]3[CH:30]=[CH:31][C:26]([C:20]4[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=4[Cl:18])=[CH:27][CH:28]=3)=[O:33])=[CH:11][C:9]=2[N:10]=1.[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]([CH3:16])[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([NH:15][C:32]([C:29]3[CH:28]=[CH:27][C:26]([C:20]4[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=4[Cl:18])=[CH:31][CH:30]=3)=[O:34])=[CH:11][C:9]=2[N:10]=1Participants
4
Reactant 2
Product 2
Procedure
The title compound is prepared by following a procedure analogous to Example 113, Step 1, using N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzooxazole-2,5-diamine (0.40 g, 1.71 mmol), and 2′,4′-dichloro-biphenyl-4-carboxylic acid (0.59 g, 2.22 mmol) to afford 2′,4′-dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzooxazol-5-yl}-amide (0.64 g, 77%). The prepared material (0.23 g, 0.473 mmol) is dissolved in EtOH and treated with 1.0 M HCl in EtOH (0.45 mL). The reaction is refluxed and the hydrochloride salt is isolated by centrifuge after precipitation with heptane as a white solid (0.18 g, 0.347 mmol, 73%). LC/MS (m/z): calcd for C25H24Cl2N4O2HCl (M+H)+: 483.4; found: 483.3.
Sources & evidence
- ORD record
- ord-4ea926c5fa4f478dbc73f2454357ec12
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838543B2
Reaction notes
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