Acetic Acid → HCID 178523066, compound

HRID 579016Notes

Reaction equation

[NH:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:8])=[CH:5][N:4]=1)[NH2:2].Cl.CN(C)[CH:22]=[C:23]([N:29]1[CH:34]=[CH:33][C:32](=[O:35])[CH:31]=[CH:30]1)[C:24](OCC)=[O:25].C(O)(=O)C>CC(O)C.CS(C)=O>[OH:25][C:24]1[N:1]([C:3]2[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[O:8])=[CH:5][N:4]=2)[N:2]=[CH:22][C:23]=1[N:29]1[CH:30]=[CH:31][C:32](=[O:35])[CH:33]=[CH:34]1

Participants

Conditions

Temperature: 20 °C

Procedure

Combined 6-hydrazinyl-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide, 1.0 HCl (30 mg, 0.105 mmol), ethyl 3-(dimethylamino)-2-(4-oxopyridin-1(4H)-yl)acrylate (37.1 mg, 0.157 mmol) and acetic acid (0.018 mL, 0.314 mmol) in 2-propanol (0.8 mL) and stirred at 20° C. for 1 hour and then at 50° C. for 16 hours and then 80° C. for 24 h. The reaction mixture was then diluted with 200 uL DMSO and purified by prep HPLC (ACN/water with formic acid) to give the title compound (11 mg, 26.6% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11-1.32 (m, 2 H) 1.62 (d, J=13.4 Hz, 2 H) 1.73-1.90 (m, 1 H) 3.20 (t, J=6.2 Hz, 2 H) 3.25 (s, 2 H) 3.86 (dd, J=11.4, 2.8 Hz, 2 H) 6.56 (br. s., 2 H) 8.19 (br. s., 2 H) 8.40 (t, J=7.7 Hz, 3 H) 8.71 (t, J=5.3 Hz, 1 H) 8.91 (s, 1 H). MS m/z 396 [M+H]+.

Workup

waitat 50° C. for 16 hours
wait80° C. for 24 h
custompurified by prep HPLC (ACN/water with formic acid)

Sources & evidence

ORD record: ord-36cfc6cbfd5044b7a416d45bef3f8b78
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040522B2

Reaction notes

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