2,2-Dimethylpropyl carbonochloridate → 4-(4'-{4-(2,4-dichloro-phenyl)-1-[4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-phenyl]-1H-imidazol-2-ylmethyl}-biphenyl-4-yl)-piperazine-1-carboxylic acid 2,2-dimethyl-propyl ester
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([N:41]4[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]4)=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[N:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]3)=[CH:16][CH:15]=2)[CH:13]=1.Cl[C:48]([O:50][CH2:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:49]>>[CH3:53][C:52]([CH3:55])([CH3:54])[CH2:51][O:50][C:48]([N:44]1[CH2:45][CH2:46][N:41]([C:38]2[CH:39]=[CH:40][C:35]([C:32]3[CH:31]=[CH:30][C:29]([CH2:28][C:11]4[N:12]([C:14]5[CH:15]=[CH:16][C:17]([N:20]6[CH2:21][C:22](=[O:27])[NH:23][S:24]6(=[O:26])=[O:25])=[CH:18][CH:19]=5)[CH:13]=[C:9]([C:3]5[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=5[Cl:1])[N:10]=4)=[CH:34][CH:33]=3)=[CH:36][CH:37]=2)[CH2:42][CH2:43]1)=[O:49]Participants
3
Reactant 2
Product 1
Procedure
5-{4-[4-(2,4-Dichloro-phenyl)-2-(4′-piperazin-1-yl-biphenyl-4-ylmethyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide (20 mg, 0.03 mmol) was treated as described in general procedure U using neopentyl chloroformate (9 mg, 0.06 mmol) to give 4-(4′-{4-(2,4-dichloro-phenyl)-1-[4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-phenyl]-1H-imidazol-2-ylmethyl}-biphenyl-4-yl)-piperazine-1-carboxylic acid 2,2-dimethyl-propyl ester.
Sources & evidence
- ORD record
- ord-c39883195b474dfebdafc52a2d384a94
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404731B2
Reaction notes
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