Acetonitrile--water (1/1) → 3-(2,4,6-trifluorobenzoyl)-6-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 908259Notes

Reaction equation

O1CCO[CH:2]1[CH2:6][N:7]([CH2:26][C:27]1[N:28]=[C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]2[CH:39]=1)[C:8]([C:10]1[NH:11][CH:12]=[C:13]([C:15](=[O:25])[C:16]2[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=2[F:24])[CH:14]=1)=[O:9].CC#N.O>CS(O)(=O)=O>[F:22][C:21]1[CH:20]=[C:19]([F:23])[CH:18]=[C:17]([F:24])[C:16]=1[C:15]([C:13]1[C:14]2[CH:2]=[CH:6][N:7]([CH2:26][C:27]3[N:28]=[C:29]4[CH:34]=[C:33]([C:35]([F:38])([F:36])[F:37])[CH:32]=[CH:31][N:30]4[CH:39]=3)[C:8](=[O:9])[C:10]=2[NH:11][CH:12]=1)=[O:25]

Participants

Conditions

Temperature: 85 °C

Procedure

The product from Step B (744 mg, 1.40 mmol) was dissolved in methanesulfonic acid (6.0 mL) and heated to 85° C. for 50 min. After cooling in an ice-water bath, the reaction mixture was taken up in 2:3 MeCN—H2O (10 mL) and purified by reverse phase HPLC (C-18 column) to give the title compound (430 mg). LC/MS: m/z 491(M+H). 1H-NMR (d6-DMSO, 500 MHz): δ 5.40 (s, 2H), 6.96 (d, 1H), 7.20 (dd, 1H), 7.33 (t, 2H), 7.57 (d, 1H), 7.88 (d, 1H), 8.01 (s, 1H), 8.03 (s, 1H), 8.71 (d, 1H), 13.09 (s, 1H).

Workup

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

Sources & evidence

ORD record: ord-52703a795c644201af11a65cace39ffe
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017605B2

Reaction notes

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