(R)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate → (R)-benzyl 4-(3-(1-(3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamido)ethyl)phenyl)piperazine-1-carboxylate

HRID 1844428Notes

Reaction equation

HRID 1844428 reaction equation
[OH:1][C:2]1[C:3](=[O:16])[N:4]([CH3:15])[C:5]2[C:10]([C:11]=1[C:12](Cl)=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:17][C@@H:18]([C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1)[CH3:19]>>[OH:1][C:2]1[C:3](=[O:16])[N:4]([CH3:15])[C:5]2[C:10]([C:11]=1[C:12]([NH:17][C@@H:18]([C:20]1[CH:21]=[C:22]([N:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:30][CH2:31]3)[CH:23]=[CH:24][CH:25]=1)[CH3:19])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 86731093(R)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate2×HCID 867310963-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonyl chloride

Product 1

HCID 86731097(R)-benzyl 4-(3-(1-(3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamido)ethyl)phenyl)piperazine-1-carboxylateYield 25%

Procedure

Following the same procedure as described for Example 3, Example 204 (12 mg, 0.022 mmol, 25% yield) was prepared as an off-white powder by using 3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonyl chloride and (R)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate (Intermediate 33). LC-MS (ESI) m/z 541 (M+H), RT=1.64 min (Method C). Orthogonal HPLC (150×4.6 mm 3.5 μm, 254 nm): Sunfire {RT=8.9 min, 95%}; Xbridge {RT=8.5 min, 93%}. 1H NMR (500 MHz, MeOD) δ ppm 7.55 (1 H, d, J=7.7 Hz), 7.46-7.50 (2 H, m), 7.36-7.41 (4 H, m), 7.30-7.34 (3 H, m), 7.26 (1 H, s), 7.22-7.24 (1 H, m), 7.13 (1 H, d, J=7.7 Hz), 7.03 (1 H, dd, J=8.1, 2.1 Hz), 5.28 (1 H, d, J=7.2 Hz), 5.17 (2 H, s), 3.82 (3H, s), 3.71 (4 H, d, J=3.6 Hz), 3.29 (4 H, d, J=5.5 Hz), 1.55 (3 H, d, J=7.2 Hz).

Workup

  1. customwas prepared as an off-white powder

Sources & evidence

ORD record
ord-06008758ad1d4aa0bf9d3660a5fc4516
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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