HCID 57744477, compound → HCID 57744516, compound

HRID 1887372Notes

Reaction equation

HRID 1887372 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]([C:19]2[S:23][C:22]([C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[O:25])=[C:21]([CH3:35])[CH:20]=2)[C:15](=[O:36])[CH:14]=1)(C(C)(C)C)(C)C>C(O)(=O)C>[F:34][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[CH2:27][NH:26][C:24]([C:22]1[S:23][C:19]([N:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:14][C:15]2=[O:36])=[CH:20][C:21]=1[CH3:35])=[O:25]

Participants

3

Reactant 1

HCID 57744477HCID 57744477, compound

Product 1

HCID 57744516HCID 57744516, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-oxopyridin-1(2H)-yl)-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide (0.368 mmol) in acetic acid (5 mL) was stirred at 60° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluted with 0-10% methanol in dichloromethane to afford the title compound as a pinkish solid in 61% yield (0.093 g): mp 135-137° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.58 (t, J=6.0 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 7.42-7.33 (m, 1H), 7.26 (s, 1H), 7.18-7.03 (m, 3H), 6.21 (dd, J=7.9, 2.7 Hz, 1H), 6.01 (d, J=2.7 Hz, 1H), 4.60 (br s, 1H), 4.42 (d, J=6.0 Hz, 2H), 4.09 (t, J=6.2 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 2.42 (s, 3H), 1.86 (p, J=6.2 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ 166.6, 162.5, 162.1 (d, JC-F=243.2 Hz), 161.0, 142.7 (d, JC-F=7.0 Hz), 138.9, 137.4, 134.8, 130.1 (d, JC-F=8.3 Hz), 127.0, 123.1 (d, JC-F=2.7 Hz), 120.4, 113.8 (d, JC-F=21.5 Hz), 113.4 (d, JC-F=20.9 Hz), 102.6, 96.6, 65.6, 56.9, 42.1, 31.4, 15.5; MS (ES+) m/z 417.3 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluted with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-5376478cc62b4986b49c88e68e33eec3
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…