Hydrochloric Acid → 2-{[7-oxo-3-(2,4,6-trifluorobenzoyl)-1,7-dihydro-6H-pyrrolo[2,3-c]pyridin-6-yl]methyl}imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 908263Notes

Reaction equation

[O:1]=[C:2]1[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:21])[C:12]3[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=3[F:20])[C:6]=2[CH:5]=[CH:4][N:3]1[CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[C:29]([C:31](N)=[O:32])[CH:28]=[CH:27][N:26]2[CH:34]=1.Cl.[OH2:36]>CC#N>[O:1]=[C:2]1[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:21])[C:12]3[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=3[F:20])[C:6]=2[CH:5]=[CH:4][N:3]1[CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[C:29]([C:31]([OH:36])=[O:32])[CH:28]=[CH:27][N:26]2[CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the product obtained in example 22 (40 mg, 0.083 mmol) suspended in H2O (0.5 mL) was added conc. HCl (0.68 mL, 8.31 mmol). The mixture was placed in a microwave reactor and heated to 100° C. for 10 min. Resulting suspension was diluted with 3:1 MeCN:H2O (2 mL) along with DMSO (1 mL) and purified by reverse phase HPLC (C-18 column) to give the title compound (29 mg). LC/MS: m/z 468(M+H). 1H-NMR (600 MHz, d6-DMSO): δ 5.45 (s, 2H), 6.98 (d, 1H), 7.32 (t, 2H), 7.53 (d, 1H), 7.61 (d, 1H), 7.88 (d, 1H), 8.15 (s, 1H), 8.17 (d, 1H), 8.71 (d, 1H).

Workup

customThe mixture was placed in a microwave reactor
customResulting suspension
customH2O (2 mL) along with DMSO (1 mL) and purified by reverse phase HPLC (C-18 column)

Sources & evidence

ORD record: ord-66548323f43a46348cc04aa372817bca
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017605B2

Reaction notes

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