Sodium Carbonate → HCID 71547641, compound

HRID 1184551Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C@@H:10]2[CH2:18][N:13]3[CH2:14][CH2:15][NH:16][CH2:17][C@@H:12]3[CH2:11]2)[N:4]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1>CS(C)=O>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([N:16]2[CH2:15][CH2:14][N:13]3[CH2:18][C@@H:10]([NH:9][C:5]4[N:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[CH:8]=[CH:7][N:6]=4)[CH2:11][C@H:12]3[CH2:17]2)=[N:29][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of Example 33 (115 mg, 0.4 mmol) and sodium carbonate (72 mg, 0.68 mmol) in dimethyl sulfoxide (0.5 mL) was added 2,5-dichloropyridine (95 mg, 0.64 mmol). The mixture was stirred at 100° C. for 2 days. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=15:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (m, 1H), 2.00-2.15 (m, 2H), 2.30-2.40 (m, 2H), 2.60 (m, 1H), 2.88-3.00 (m, 3H), 4.20-4.40 (m, 3H), 6.89 (d, 1H, J=7 Hz), 6.98 (m, 1H), 7.58 (d, 1H, J=7 Hz), 8.04 (m, 1H), 8.06 (s, 1H), 8.60 (m, 1H); MS (ESI) m/z 399 (M+H)+.

Workup

customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol=15:1)

Sources & evidence

ORD record: ord-aedc3cc6fb914f45a9da08559cb27d13
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669255B2

Reaction notes

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