Hydrochloric Acid → HCID 18188257, compound

HRID 1357817Notes

Reaction equation

HRID 1357817 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][N:12]=[C:11]3[C:14]4[C:19]([C:20](=[O:21])[C:10]=23)=[C:18]([NH:22]C(=O)C)[CH:17]=[CH:16][CH:15]=4)=[CH:5][CH:4]=1.Cl>CO>[NH2:22][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:20](=[O:21])[C:10]1[C:11]2=[N:12][N:13]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178489087HCID 178489087, compound

Product 1

HCID 18188257HCID 18188257, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of N-[3-(4-Methoxy-phenyl)-4-oxo-2,4-dihydro-indeno[1,2-c]pyrazol-5-yl]-acetamide (as produced according to Nugiel, D. A.; Etzkorn, A. M.; Vidwans, A.; Benfield, P. A.; Boisclair, M.; Burton, C. R.; Cox, S.; Czerniak, P. M.; Doleniak, D.; Seitz, S. P. J. Med. Chem. 2001, 44, 1334-1336) (1.0 g, 3.0 mmol) in MeOH (10 mL) was treated with concentrated HCl (1 mL) and heated to reflux. After stirring the mixture for 2 h the reaction was cooled and the product was collected by filtration and obtained as a greenish solid (0.7 g, 81%). mp 273° C.; NMR (DMSO-d6) δ13.6 (bs, 1 H), 8.3 (d, J=8.4 Hz, 1 H), 8.1 (d, J=8.8 Hz, 2 H), 7.5 (t, J=7.7 Hz 1 H), 7.2 (d, J=7.0 Hz, 1 H), 7.1 (d, J=8.8 Hz, 2 H), 3.8 (s, 3 H); HRMS m/e calc'd for C17H14N3O2 (M+H): 292.1086, found: 292.1080.

Workup

  1. customas produced
  2. temperatureheated to reflux
  3. temperaturewas cooled
  4. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-70c17fda3c2d46008a417b7236e3870f
Source dataset
uspto-grants-2003_07
Patent number
US06593356B2

Reaction notes

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