Oxalyl chloride → 4'-Fluoro-biphenyl-4-carboxylic acid {2-[methyl-(1-methyl-pyrrolidin-3-yl)-amino]-benzothiazol-6-yl}-amide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:20])=O.[CH3:23][N:24]([CH:35]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]1)[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:20].[CH3:23][N:24]([CH:35]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]1)[C:25]1[S:26][C:27]2[CH:33]=[C:32]([NH:34][C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:13][CH:12]=3)=[O:16])[CH:31]=[CH:30][C:28]=2[N:29]=1.[CH3:23][N:24]([CH:35]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]1)[C:25]1[S:26][C:27]2[CH:33]=[C:32]([NH:34][C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:13][CH:12]=3)=[O:15])[CH:31]=[CH:30][C:28]=2[N:29]=1Participants
5
Reactant 3
Product 2
Procedure
The title compound is prepared by following Method C, using 4′-fluoro-biphenyl-4-carboxylic acid (3.46 g, 16.01 mmol), oxalyl chloride (4.65 mL, 53.36 mmol) and isomer-2 of N*2*-methyl-N*2*-(1-methyl-pyrrolidin-3-yl)-benzothiazole-2,6-diamine (2.80 g, 10.76 mmol) to give 4′-fluoro-biphenyl-4-carboxylic acid {2-[methyl-(1-methyl-pyrrolidin-3-yl)-amino]-benzothiazol-6-yl}-amide (2.41 g, 49%). The material is dissolved in THF (100 mL), and 1.0 M HCl in EtOH is added to adjusted the pH to 1. The resulting solid is collected and recrystallized from EtOH/Heptane to give 2.03 g (78%). LC/MS: Retention time=5.06 min; (m/z): calcd for, C26H25FN4OS (M+H)+: 461.6; found: 461.0.
Sources & evidence
- ORD record
- ord-04ed392b7cca421b90f8daaca5a6c193
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838543B2
Reaction notes
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