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

HRID 1844429Notes

Reaction equation

HRID 1844429 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 86731092(S)-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 86731098(S)-benzyl 4-(3-(1-(3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamido)ethyl)phenyl)piperazine-1-carboxylate

Procedure

Following the same procedure as described for Example 3, Example 205 was prepared as an off-white powder by using 3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonyl chloride and (S)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate (Intermediate 34). LC-MS (ESI) m/z 541 (M+H), RT=2.00 min (Method B). Orthogonal HPLC (150×4.6 mm 3.5 μm, 254 nm): Sunfire {RT=8.9 min, 93%}; Xbridge {RT=8.5 min, 92%}.

Workup

  1. customwas prepared as an off-white powder

Sources & evidence

ORD record
ord-b328e4eea7244f87814587da83659581
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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