Hydrochloric Acid → 3-[4-fluoro-3-[2-oxo-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]acetyl]-1H-pyrrolo[2,3-c]pyridin-7-yl]-1H-pyrazole-5-carboxylic acid

HRID 1157763Notes

Reaction equation

[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[NH:10][N:9]=2)=[C:4]2[NH:18][CH:19]=[C:20]([C:21](=[O:41])[C:22](=[O:40])[N:23]3[CH2:28][CH2:27][N:26]([C:29]4[N:33]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[N:32]=[N:31][N:30]=4)[CH2:25][CH2:24]3)[C:3]=12.O.[OH-].[Li+].Cl>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[NH:10][N:9]=2)=[C:4]2[NH:18][CH:19]=[C:20]([C:21](=[O:41])[C:22](=[O:40])[N:23]3[CH2:28][CH2:27][N:26]([C:29]4[N:33]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:32]=[N:31][N:30]=4)[CH2:25][CH2:24]3)[C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a rb flask containing ethyl 3-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-pyrazole-5-carboxylate (0.058 g, 0.10 mmol) in DMF (5 mL) and water (5 mL) was added lithium hydroxide monohydrate (0.044 g, 1.05 mmol). The mixture was heated to 100° C. for 21.5 h. The mixture was cooled to rt, and HCl was added to PH=1. Solids precipitated out of solution, and were collected by filtration to give the title compound as a yellow solid (0.03 g). LCMS: m/e 531.15 (M+H)+, ret time 2.10 min (method 2). 1H NMR (500 MHz, DMSO-D6) δ ppm 14.37 (s, 1H) 13.58 (s, 1H) 12.23 (s, 1H) 8.21-8.42 (m, 2H) 7.52-7.77 (m, 5H) 7.35 (s, 1H) 3.08-3.76 (m, 8H).

Workup

temperatureThe mixture was cooled to rt
customSolids precipitated out of solution
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-e5a733d1f424408a8c9af0326ef86852
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807676B2

Reaction notes

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