Hydrochloric Acid → HCID 178524170, compound

HRID 408697Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]2[N:9](COCCOC)[C:10]([N:12]3[CH:16]=[C:15]([C:17]([O:19]CC)=[O:18])[CH:14]=[N:13]3)=[N:11][C:7]=2[CH:6]=1)=[O:4].Cl>C(O)(=O)C>[C:17]([C:15]1[CH:14]=[N:13][N:12]([C:10]2[NH:9][C:8]3[CH:28]=[CH:29][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)[CH:16]=1)([OH:19])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 2-(4-ethoxycarbonyl-pyrazol-1-yl)-1-(2-methoxy ethoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (0.150 g, 0.373 mmol) and acetic acid (4.5 mL) was added aqueous hydrochloric acid (6M, 4.5 mL). The reaction mixture was heated to 100° C. for 18 h and then cooled to 23° C. The resulting precipitate was collected to yield the titled compound (0.30 mg, 30% yield). MS (ESI/CI): mass calcd. for C12H8N4O4, 272.1; m/z found, 273.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 8.94 (s, 1H), 8.32 (s, 1H), 8.14 (s, 1H), 7.87 (dd, J=8.4, 1.5 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H).

Workup

temperaturecooled to 23° C
customThe resulting precipitate was collected

Sources & evidence

ORD record: ord-04a515b7a0eb4c96975fc03b30839b5a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759345B2

Reaction notes

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