N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine → HCID 11656851, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][CH:14]=1.[CH3:22][N:23]([CH3:38])[CH2:24][CH2:25][N:26]([CH3:37])[C:27]1[S:28][C:29]2[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:30]=2[N:31]=1>>[ClH:1].[CH3:22][N:23]([CH3:38])[CH2:24][CH2:25][N:26]([CH3:37])[C:27]1[S:28][C:29]2[CH:35]=[C:34]([NH:36][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:3]4[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=4[Cl:1])=[CH:14][CH:15]=3)=[O:20])[CH:33]=[CH:32][C:30]=2[N:31]=1.[CH3:22][N:23]([CH3:38])[CH2:24][CH2:25][N:26]([CH3:37])[C:27]1[S:28][C:29]2[CH:35]=[C:34]([NH:36][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:3]4[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=4[Cl:1])=[CH:14][CH:15]=3)=[O:20])[CH:33]=[CH:32][C:30]=2[N:31]=1Participants
4
Procedure
The title compound is prepared by following Method A, using 2′-chloro-4′-trifluoromethoxy-biphenyl-4-carboxylic acid (0.057 g, 0.18 mmol), and N*2*-(2-Dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (0.38 g, 0.15 mmol) to afford 2′-chloro-4′-trifluoromethoxy-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (0.033 g, 40%). The material is dissolved in EtOH and treated with 1.0 M HCl in EtOH (0.06 mL). Heptane is added and the resulting precipitate is collected to give 0.028 g (78%) of the hydrochloride salt. LC/MS, Retention time=5.38 nm; (m/z): calcd for C26H24ClF3N4O2S (M+H)+: 549.0; found: 549.0.
Sources & evidence
- ORD record
- ord-3c53c85a9a654a8ebb0fd8521a26a862
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838543B2
Reaction notes
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