Diisopropylethylamine → HCID 178522808, compound

HRID 526549Notes

Reaction equation

CN(C)[CH:3]=[C:4]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[C:5](OCC)=[O:6].[CH2:17]([NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[N:28][CH:27]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH2:17]([NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:5]([OH:6])=[C:4]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[CH:3]=[N:33]2)=[N:28][CH:27]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Combined ethyl 3-(dimethylamino)-2-(pyridin-4-yl)acrylate (40.0 mg, 0.182 mmol) and N-benzyl-6-hydrazinylnicotinamide (33.8 mg, 0.140 mmol) in 2-propanol (0.698 mL) and stirred for 18 hours at room temperature. Hunig's base (0.219 mL, 1.257 mmol) was then added and the reaction was stirred for 24 hours at 50° C. The reaction mixture was then purified by preparative HPLC (SunFire™ C18, 5 μm, ID 30 mm×75 mm) eluting with ACN (with 0.035% TFA) in water (with 0.05% TFA) to give the title compound (18.5 mg, 35.7%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.58 (d, J=5.8 Hz, 2H) 7.33 (dq, J=8.5, 4.3 Hz, 1H) 7.37-7.45 (m, 4H) 8.28 (d, J=6.3 Hz, 2H) 8.45 (d, J=7.1 Hz, 2H) 8.49-8.58 (m, 2H) 8.63 (s, 1H) 8.99 (s, 1H) 9.33 (t, J=5.9 Hz, 1H). MS m/z [M+H]+ 372.4.

Workup

customThe reaction mixture was then purified by preparative HPLC (SunFire™ C18, 5 μm, ID 30 mm×75 mm)
washeluting with ACN (with 0.035% TFA) in water (with 0.05% TFA)

Sources & evidence

ORD record: ord-84e9630f4d994011b7b94f4e1bc1092f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345713B2

Reaction notes

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