N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine → HCID 57771724, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1.[CH3:21][N:22]([CH3:37])[CH2:23][CH2:24][N:25]([CH3:36])[C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:29]=2[N:30]=1>>[ClH:1].[CH3:21][N:22]([CH3:37])[CH2:23][CH2:24][N:25]([CH3:36])[C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH:35][C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:3]4[CH:4]=[CH:5][C:6]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:7][C:2]=4[Cl:1])=[CH:17][CH:16]=3)=[O:20])[CH:32]=[CH:31][C:29]=2[N:30]=1.[CH3:21][N:22]([CH3:37])[CH2:23][CH2:24][N:25]([CH3:36])[C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH:35][C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:3]4[CH:4]=[CH:5][C:6]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:7][C:2]=4[Cl:1])=[CH:13][CH:14]=3)=[O:19])[CH:32]=[CH:31][C:29]=2[N:30]=1Participants
4
Procedure
The title compound is prepared by following Method A, using 2′-chloro-4′-isopropoxy-biphenyl-4-carboxylic acid (0.35 g, 1.21 mmol), and N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (0.23 g, 0.93 mmol) to afford 2′-chloro-4′-isopropoxy-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (0.23 g, 48%). The material is dissolved in EtOH and treated with 1.0 M HCl in EtOH (0.44 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 0.24 g (96%) of the hydrochloride salt. LC/MS, Retention time=5.73 min; (m/z): calcd for C28H31ClN4O2S: 523.1; found: 523.0.
Sources & evidence
- ORD record
- ord-37e851c2f87b4b848e08e1118af1276a
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838543B2
Reaction notes
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