Hydrochloric Acid → HCID 178477330, compound

HRID 1707656Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:27]#[N:28])[N:5]([C:7]2[CH:26]=[CH:25][C:10]([CH2:11][N:12]3[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH3:21])=[C:15]4[N:14]=[C:13]3[S:22][CH2:23][CH3:24])=[CH:9][CH:8]=2)[CH:6]=1.[N-:29]=[N+:30]=[N-:31].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCN(C)C1=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:27]2[NH:31][N:30]=[N:29][N:28]=2)[N:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH3:21])=[C:15]4[N:14]=[C:13]3[S:22][CH2:23][CH3:24])=[CH:25][CH:26]=2)[CH:6]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a mixture of 3-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (846 mg) in 1,3-dimethyl-2-imidazolidinone (10 ml) was added sodium azide (539 mg) and triethylamine hydrochloride (1.425 g) and stirred at 135° C. for 24 hours. The reaction mixture was poured into ice-water and the pH value was adjusted to 4 with 7% hydrochloric acid, extracted with ethyl acetate (twice) and the organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was crystallized from methyl cyanide and washed hot methyl cyanide to give 3-[4-[4-chloro-2-(1H-tetrazol-5-yl)-1-pyrrolyl]-benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine(766 mg) as a brown solid. mp: 88°-90° C.

Workup

extractionextracted with ethyl acetate (twice) and the organic layer
washwas washed with water
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was crystallized from methyl cyanide
washwashed hot methyl cyanide

Sources & evidence

ORD record: ord-fccb61eba3254dec942e4a94da6baf49
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05354759

Reaction notes

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