Boronic Acid → 5-{3-[2-[4-(3-Cyclohexyl-propenyl)-benzyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide

HRID 2240766Notes

Reaction equation

HRID 2240766 reaction equation
[CH:1]1([CH2:7][C:8]#[CH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B1C2CCCC1CCC2.B(O)O.Br[C:23]1[CH:56]=[CH:55][C:26]([CH2:27][C:28]2[N:29]([C:41]3[CH:42]=[C:43]([N:47]4[S:51](=[O:53])(=[O:52])[NH:50][C:49](=[O:54])[CH2:48]4)[CH:44]=[CH:45][CH:46]=3)[CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=3[Cl:40])[N:32]=2)=[CH:25][CH:24]=1>C1COCC1>[CH:1]1([CH2:7][CH:8]=[CH:9][C:23]2[CH:56]=[CH:55][C:26]([CH2:27][C:28]3[N:29]([C:41]4[CH:42]=[C:43]([N:47]5[S:51](=[O:52])(=[O:53])[NH:50][C:49](=[O:54])[CH2:48]5)[CH:44]=[CH:45][CH:46]=4)[CH:30]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=4[Cl:40])[N:32]=3)=[CH:25][CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 61668Boronic AcidHCID 789669-Borabicyclo(3.3.1)nonaneHCID 87265(Prop-2-yn-1-yl)cyclohexaneHCID 593055095-{3-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide

Product 1

HCID 685855345-{3-[2-[4-(3-Cyclohexyl-propenyl)-benzyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-cyclohexyl-1-propyne (145 μL, 1 mmol) in 2 mL dry THF at 0° C. was added 2 mL 0.5 M 9-BBN solution in THF. The resulting solution was stirred at room temperature under nitrogen for 4 hr. Then it was condensed under vacuum and used as boronic acid derivative according to general procedure G, reacting with 5-{3-[2-(4-bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide (119 mg, 0.2 mmol) to give 5-{3-[2-[4-(3-cyclohexyl-propenyl)-benzyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide.

Workup

  1. customcondensed under vacuum

Sources & evidence

ORD record
ord-5eabcdaf82f1409eba0d2091be2d080b
Source dataset
uspto-grants-2010_05
Patent number
US07723369B2

Reaction notes

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