Methanesulfonic 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-carboxamide

HRID 908262Notes

Reaction equation

HRID 908262 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([CH2:12][N:13]([CH2:32][CH:33]3OCCO3)[C:14]([C:16]3[NH:17][CH:18]=[C:19]([C:21](=[O:31])[C:22]4[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=4[F:30])[CH:20]=3)=[O:15])[N:11]=[C:5]2[CH:4]=1)#[N:2].CS(O)(=O)=[O:40]>CC#N.O>[O:15]=[C:14]1[C:16]2[NH:17][CH:18]=[C:19]([C:21](=[O:31])[C:22]3[C:23]([F:30])=[CH:24][C:25]([F:29])=[CH:26][C:27]=3[F:28])[C:20]=2[CH:33]=[CH:32][N:13]1[CH2:12][C:10]1[N:11]=[C:5]2[CH:4]=[C:3]([C:1]([NH2:2])=[O:40])[CH:8]=[CH:7][N:6]2[CH:9]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 58024818N-[(7-cyanoimidazo[1,2-a]pyridine-2-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide

Product 1

HCID 445467272-{[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-carboxamide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
95 °C

Procedure

The product from step B (430 mg, 0.884 mmol) was dissolved in methanesulfonic acid (2.0 mL) and heated to 95° C. in an oil bath for 25 min. After cooling in an ice-water bath, the reaction mixture was diluted with 2:3 MeCN—H2O (3 mL) and purified by reverse phase HPLC (C-18 column) to give the title compound (174 mg). LC/MS: m/z 467(M+H). 1H-NMR (d6-DMSO, 500 MHz): δ 5.46 (s, 2H), 7.01 (d, 1H), 7.33 (t, 2H), 7.58-7.59 (m, 2H), 7.61 (s, 1H), 7.79 (s, 1H), 7.91 (d, 1H) 8.12 (d, 1H), 8.33 (s, 1H), 8.72 (d, 1H), 13.12 (s, 1H).

Workup

  1. temperatureAfter cooling in an ice-water bath
  2. custompurified by reverse phase HPLC (C-18 column)

Sources & evidence

ORD record
ord-1db2399fd9d9431fb163567bd309a406
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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