Phenylmethyl 3,5-dioxo-1-piperidinecarboxylate → HCID 136242927, compound

HRID 1775226Notes

Reaction equation

HRID 1775226 reaction equation
Br[C:2]1[C:11]([NH2:12])=[CH:10][C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6]C)=O.O=[C:15]1[CH2:20]C(=O)CN(C(OCC2C=CC=CC=2)=O)[CH2:16]1.[CH3:32][N:33]1[CH2:45][C:44]2NC3C=CC=C4C(=O)[NH:47][N:48]=[C:35]([C:36]=2C=34)[CH2:34]1>>[CH2:32]([N:33]1[CH2:45][C:44]2[NH:12][C:11]3[CH:10]=[C:9]([F:13])[CH:8]=[C:3]4[C:4](=[O:6])[NH:47][N:48]=[C:35]([C:36]=2[C:2]=34)[CH2:34]1)[CH2:16][CH2:15][CH3:20]

Participants

4

Reactant 3

HCID 49761164Phenylmethyl 3,5-dioxo-1-piperidinecarboxylateHCID 63022281methyl 3-amino-2-bromo-5-fluorobenzoateHCID 136242914HCID 136242914, compound

Product 1

HCID 136242927HCID 136242927, compound

Procedure

Compound 59 was prepared from methyl 2-bromo-5-fluoro-3-aminobenzoate and benzyl 3,5-dioxopiperidine-1-carboxylate according to the procedures similar to those for Compound 44. 1H NMR (DMSO-d6) δ 11.8 (s, 1H), 10.1 (s, 1H), 7.36 (dd, 1H, J=2.4, 9.6 Hz), 7.19 (dd, 1H, J=2.4, 10.2 Hz), 3.80 (s, 2H), 3.30 (s, 2H), 2.54-2.57 (m, 2H), 1.47-1.50 (m, 2H), 1.30-1.34 (m, 2H), and 0.91 (t, 3H, J=7.2 Hz). MS (ESI) m/e [M+1]+ 301.

Sources & evidence

ORD record
ord-ba201688058b41fca8a7cfba43df923d
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

Loading…