{4-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenylamino}-acetic acid methyl ester → HCID 68583516, compound

HRID 2240759Notes

Reaction equation

HRID 2240759 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[N:14]=[C:13]2[CH2:25][C:26]2[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=2)=[CH:8][CH:7]=1.[CH:34]1([CH2:39][CH:40]([C:42]2[CH:47]=[CH:46][C:45](B3OC(C)(C)C(C)(C)O3)=[CH:44][CH:43]=2)[OH:41])[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH3:1][O:2][C:3](=[O:33])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[N:14]=[C:13]2[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:45]3[CH:46]=[CH:47][C:42]([CH:40]([OH:41])[CH2:39][CH:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)=[CH:43][CH:44]=3)=[CH:28][CH:27]=2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 68583535{4-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenylamino}-acetic acid methyl esterHCID 68585558HCID 68585558, compound

Product 1

HCID 68583516HCID 68583516, compound

Procedure

{4-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenylamino}-acetic acid methyl ester (433 mg, 0.79 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 give {4-[2-[4′-(2-cyclopentyl-1-hydroxy-ethyl)-biphenyl-4-ylmethyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenylamino}-acetic acid methyl ester. The product benzyl alcohol was reduced according to general procedure AA and the reduced product was treated following general procedure F to give 5-{4-[2-[4′-(2-cyclopentyl-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-d718d22b7f944796ac129aee4803ae2c
Source dataset
uspto-grants-2010_05
Patent number
US07723369B2

Reaction notes

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