Hydrochloric Acid → HCID 58305709, compound

HRID 2362226Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[N:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[N:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])[C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:31]=[N:32][NH:33][N:19]=3)=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To 25 mL vial which contained 3-[1-(4-carbamoyl-2-methyl-phenyl)-5-(4-cyano-phenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (26A) (50 mg, 0.12 mmol.) in DMF (4 mL) was added sodium azide (40 mg, 0.6 mmol.) and ammonium chloride (40 mg, 0.8 mmol.) at rt. The vial was sealed and the reaction mixture was heated to 100° C. and stirred for 16 h. The reaction mixture was cooled to rt and poured into 30 mL ice-water solution. The aqueous solution was acidified with aq HCl (1 N) to pH=1-2, the solid which formed was filtered out, washed with water (25 mL), dried over air to afford the desired compound 3-{1-(4-Carbamoyl-2-methyl-phenyl)-5-[4-(2H-tetrazol-5-yl)-phenyl]-1H-pyrrol-2-yl}-propionic acid ethyl ester (26B) (27 mg, 50% yield).

Workup

customThe vial was sealed
temperatureThe reaction mixture was cooled to rt
customthe solid which formed
filtrationwas filtered out
washwashed with water (25 mL)
customdried over air

Sources & evidence

ORD record: ord-d7538541df254fb5838aaafdc6393780
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691816B2

Reaction notes

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