Hydrochloric Acid → HCID 178477325, compound

HRID 1792535Notes

Reaction equation

[CH2:1]([S:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7]2[CH:16]=[C:17]([C:20]3[C:21]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)=[N:22][N:23](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:24]=3)[CH:18]=[CH:19][C:6]=2[N:5]=1)[CH3:2].[ClH:51]>>[ClH:51].[ClH:51].[CH2:1]([S:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7]2[CH:16]=[C:17]([C:20]3[C:21]([C:44]4[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=4)=[N:22][NH:23][CH:24]=3)[CH:18]=[CH:19][C:6]=2[N:5]=1)[CH3:2]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 22032176HCID 22032176, compound

Product 1

HCID 178477325HCID 178477325, compound

Procedure

A solution mixture of 7.2 g 2-(ethylsulfanyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole obtained in Production Example 73, 3.5 g 4-fluorophenylboronic acid, 3.4 g copper (II) acetate, 2.0 mL pyridine, 4.6 g of 4 Å molecular sieves and 140 mL dichloromethane was stirred at room temperature for 96 hours. The reaction mixture was filtered through Celite, the solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give 1.06 g 2-(ethylsulfanyl)-1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole as colorless crystals. 30 mg of 2-(ethylsulfanyl)-1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole was subjected to deprotection of the trityl group and converted into the corresponding hydrochloride by the same method as in Example 67, to give 13 mg of the title compound as colorless crystals.

Sources & evidence

ORD record: ord-ec86ff751bfe49ec8abc8dd454631803
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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