Aniline → 5-{3-[2-[4'-(2-Cyclopentyl-1-hydroxy-ethyl)-biphenyl-4-ylmethyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidin-3-one-1,1-dioxide

HRID 2240757Notes

Reaction equation

HRID 2240757 reaction equation
CC(NC1C=C(N)C=CC=1)=O.NC1C=CC=CC=1.[Br:19][C:20]1[CH:53]=[CH:52][C:23]([CH2:24][C:25]2[N:26]([C:38]3[CH:39]=[C:40]([N:44]4[S:48](=[O:50])(=[O:49])[NH:47][C:46](=[O:51])[CH2:45]4)[CH:41]=[CH:42][CH:43]=3)[CH:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])[N:29]=2)=[CH:22][CH:21]=1.BrN1NC(=O)CS1.[CH:61]1([CH2:66][CH:67]([C:69]2[CH:74]=[CH:73][C:72](B3OC(C)(C)C(C)(C)O3)=[CH:71][CH:70]=2)[OH:68])[CH2:65][CH2:64][CH2:63][CH2:62]1>>[Br:19][C:20]1[CH:53]=[CH:52][C:23]([CH2:24][C:25]2[N:26]([C:38]3[CH:39]=[C:40]([NH2:44])[CH:41]=[CH:42][CH:43]=3)[CH:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])[N:29]=2)=[CH:22][CH:21]=1.[CH:61]1([CH2:66][CH:67]([C:69]2[CH:70]=[CH:71][C:72]([C:20]3[CH:21]=[CH:22][C:23]([CH2:24][C:25]4[N:26]([C:38]5[CH:39]=[C:40]([N:44]6[S:48](=[O:50])(=[O:49])[NH:47][C:46](=[O:51])[CH2:45]6)[CH:41]=[CH:42][CH:43]=5)[CH:27]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=5[Cl:37])[N:29]=4)=[CH:52][CH:53]=3)=[CH:73][CH:74]=2)[OH:68])[CH2:65][CH2:64][CH2:63][CH2:62]1

Participants

7

Reactant 5

HCID 6115AnilineHCID 7604m-AminoacetanilideHCID 593055095-{3-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxideHCID 68585558HCID 68585558, compoundHCID 86614319Bromo-thiadiazolidinone

Product 2

HCID 593054725-{3-[2-[4'-(2-Cyclopentyl-1-hydroxy-ethyl)-biphenyl-4-ylmethyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidin-3-one-1,1-dioxideHCID 685831933-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenylamine

Procedure

3-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenylamine was prepared from 3-aminoacetanilide according to general procedure M, then the aniline was converted to 5-{3-[2-(4-bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidin-3-one-1,1-dioxide as described in general procedures E and F. The bromo-thiadiazolidinone (100 mg, 0.17 mmol) was coupled with 2-cyclopentyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanol according to general procedure G to provide 5-{3-[2-[4′-(2-cyclopentyl-1-hydroxy-ethyl)-biphenyl-4-ylmethyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidin-3-one-1,1-dioxide.

Sources & evidence

ORD record
ord-851521f58a0b4f3787b61c54fe13c8f0
Source dataset
uspto-grants-2010_05
Patent number
US07723369B2

Reaction notes

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