Sodium Carbonate → HCID 71548274, compound

HRID 1184571Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[CH2:17][N:12]3[CH2:13][CH2:14][NH:15][CH2:16][C@@H:11]3[CH2:10]2)=[N:6][CH:7]=1.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[CH2:17][N:12]3[CH2:13][CH2:14][N:15]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=4)[CH2:16][C@@H:11]3[CH2:10]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of Example 57 (76.2 mg, 0.3 mmol) in dimethyl sulfoxide (0.3 mL) was added 2-chloro-6-(trifluoromethyl)pyridine (87 mg, 0.48 mmol) and sodium carbonate (64 mg, 0.6 mmol). The mixture was stirred at 100° C. for 4 days and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.90 (m, 2H), 2.22-2.36 (m, 3H), 2.58 (m, 1H), 2.90-3.08 (m, 2H), 3.62 (m, 1H), 4.30 (m, 1H), 4.44 (m, 1H), 5.31 (m, 1H), 6.83 (d, 1H, J=7 Hz), 7.05 (d, 1H, J=7 Hz), 7.15 (d, 1H, J=7 Hz), 7.78 (m, 2H), 8.22 (s, 1H); MS (ESI) m/z 399 (M+H)+.

Workup

concentrationconcentrated
customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1)

Sources & evidence

ORD record: ord-a4d8a4f862974a9ab576aa2d4a3f9d44
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669255B2

Reaction notes

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