Pyridinium chloride → HCID 178425438, compound

HRID 876024Notes

Reaction equation

[CH3:1][C:2]1([CH3:36])[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3[N:13]=[C:14]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)=[CH:20][N:19]=4)[N:15]=[CH:16][C:11]=3[C:10]3[CH:30]=[CH:31][N:32]=[C:33]([O:34]C)[C:9]2=3)[CH2:4][CH2:3]1.Cl.N1C=CC=CC=1>C(#N)C.O>[CH3:1][C:2]1([CH3:36])[CH2:3][CH2:4][CH:5]([N:8]2[C:12]3[N:13]=[C:14]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]5)=[CH:20][N:19]=4)[N:15]=[CH:16][C:11]=3[C:10]3[CH:30]=[CH:31][N:32]=[C:33]([OH:34])[C:9]2=3)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of compound 331 (90 mg, 153 μmol) and pyridine hydrochloride (177 mg, 1.53 mmol) was heated at 170° C. (oil bath) for 4 h. After cooling to room temperature, the mixture was subjected to reverse phase preparative HPLC (acetonitrile/water containing 0.1% TFA each, 40 min from 10 to 50%). Lyophilization provided compound 334 (150 mg) as a yellow solid (TFA salt). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.66 (1 H, br. s.), 9.30 (1 H, s), 8.80 (2 H, br. s.), 8.05 (1 H, d, J=2.7 Hz), 7.92 (1 H, d, J=8.6 Hz), 7.75 (1 H, br. s.), 7.28 (1 H, t, J=5.7 Hz), 7.06 (1 H, d, J=6.3 Hz), 3.33-3.43 (4 H, m), 3.29 (5 H, d, J=1.6 Hz), 2.71-2.94 (2 H, m), 1.47-1.70 (4 H, m), 1.31-1.45 (2 H, m), 1.16 (3 H, s), 0.99 (3 H, s). LCMS-ESI (POS), M/Z, M+1: Found 473.2.

Workup

temperatureAfter cooling to room temperature
custom40 min

Sources & evidence

ORD record: ord-946eb453eeca409d91c124acc6789d6b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980903B2

Reaction notes

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