2'-Chloro-4'-ethoxy[1,1'-biphenyl]-4-carboxylic acid → HCID 57771710, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1.[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][N:24]([CH3:35])[C:25]1[S:26][C:27]2[CH:33]=[C:32]([NH2:34])[CH:31]=[CH:30][C:28]=2[N:29]=1>>[ClH:1].[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][N:24]([CH3:35])[C:25]1[S:26][C:27]2[CH:33]=[C:32]([NH:34][C:17]([C:14]3[CH:13]=[CH:12][C:11]([C:3]4[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[CH:7][C:2]=4[Cl:1])=[CH:16][CH:15]=3)=[O:19])[CH:31]=[CH:30][C:28]=2[N:29]=1.[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][N:24]([CH3:35])[C:25]1[S:26][C:27]2[CH:33]=[C:32]([NH:34][C:17]([C:14]3[CH:15]=[CH:16][C:11]([C:3]4[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[CH:7][C:2]=4[Cl:1])=[CH:12][CH:13]=3)=[O:18])[CH:31]=[CH:30][C:28]=2[N:29]=1Participants
4
Procedure
The title compound is prepared by following Method A, using 2′-chloro-4′-ethoxy-biphenyl-4-carboxylic acid (0.48 g, 1.73 mmol), and N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (0.33 g, 1.33 mmol) to afford 2′-chloro-4′-ethoxy-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (0.48 g, 71%). The material is dissolved in EtOH and treated with 1.0 M HCl in EtOH (0.94 mL). Organic solvent is removed in vacuo, the residue is dissolved in i-PrOH, heptane is added and the resulting precipitate is collected to give 0.43 g (84%) of the hydrochloride salt. LC/MS: Retention time=5.51 min; (m/z): calcd for C27H29ClN4O2S (M+H)+: 510.1; found: 510.0.
Sources & evidence
- ORD record
- ord-2a7df91252ff47e384906bedff387544
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838543B2
Reaction notes
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