Ethyl 3-bromopropionate → HCID 58168020, compound

HRID 1029280Notes

Reaction equation

HRID 1029280 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([NH:1][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][C:4]=2[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

3

Reactant 2

HCID 68320Ethyl 3-bromopropionateHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168020HCID 58168020, compoundYield 66.3%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (100 mg, 0.47 mmol) and ethyl 3-bromopropanoate (0.01 mL, 0.57 mmol) to provide 459 (97 mg, 66% yield) as a white powder. LC-MS (M+H=312, obsd.=312). 1H NMR (400 MHz, DMSO-D6) δ 8.54 (dd, J=6.3, 14.0, 1H), 8.03 (d, J=8.7, 1H), 7.29 (m, 2H), 6.88 (d, J=6.8, 1H), 6.17 (s, 1H), 4.68 (t, J=7.5, 2H), 4.01 (q, J=7.1, 2H), 2.63 (dd, J=21.6, 29.0, 4H), 1.10 (t, J=7.1, 3H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-980143b9a72c444384c50f638e399b0d
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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