Sodium Hydroxide → HCID 178441490, compound

HRID 1586831Notes

Reaction equation

[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[C:25]([Cl:27])[C:24]([Cl:28])=[C:23]3[C:29]#[N:30])=[CH:18][CH:17]=2)[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:35]=[N+:36]=[N-:37])(C)C.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[C:25]([Cl:27])[C:24]([Cl:28])=[C:23]3[C:29]3[NH:37][N:36]=[N:35][N:30]=3)=[CH:18][CH:17]=2)[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-butyl-3-[4-(3,4-dichloro-2-cyano-1-pyrrolyl)benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (490 mg) and trimethyltin azide (690 mg) in xylene (5 ml) was stirred at 120° C. for 22 hours. After cooled to ambient temperature, the mixture was treated with aqueous 1N sodium hydroxide (10 ml) for 4 hours. The suspension was filtered. The filtrate was washed with diisopropyl ether, adjusted to pH 4 with aqueous 1N-hydrochloric acid, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution by methanol/dichloromethane=1/8) to give 2-butyl-3-[4-[3,4-dichloro-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (516 mg) as an amorphous solid.

Workup

temperatureAfter cooled to ambient temperature
filtrationThe suspension was filtered
washThe filtrate was washed with diisopropyl ether
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (elution by methanol/dichloromethane=1/8)

Sources & evidence

ORD record: ord-62efe70818f94aa288b114af41286a04
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215994

Reaction notes

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