Butanoic acid, 3-bromo-, ethyl ester → HCID 58168132, compound

HRID 1029281Notes

Reaction equation

HRID 1029281 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[CH:18]([CH3:25])[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][CH2:25][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 95424Butanoic acid, 3-bromo-, ethyl esterHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168132HCID 58168132, compoundYield 13%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (160 mg, 0.76 mmol) and ethyl 3-bromobutanoate (0.01 mL, 0.91 mmol) to provide 460 (32 mg, 13% yield) as a white powder. LC-MS (M+H=326, obsd.=326). 1H NMR (400 MHz, DMSO-D6) δ 8.53 (ddd, J=1.7, 6.4, 9.7, 2H), 8.03 (d, J=8.6, 1H), 7.27 (m, 2H), 6.88 (dd, J=2.1, 8.7, 1H), 6.14 (s, 2H), 4.47 (t, J=6.9, 2H), 3.97 (q, J=7.1, 2H), 2.33 (t, J=7.4, 2H), 1.95 (p, J=7.3, 2H), 1.12 (t, J=7.1, 3H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-dafbde8b4ea740e7ba2f758320d52276
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…