HCID 53718217, compound → Cyclopentyl(S)-2-(3-{4-[6-Amino-5-(4-fluorobenzoyl)-2-oxo-2H-pyridin-1-yl]phenoxy}propylamino)-4-methylpentanoate

HRID 1667371Notes

Reaction equation

HRID 1667371 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][CH:9]=2)[C:6](=[O:23])[CH:5]=[CH:4][C:3]=1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.[CH:33]1([O:38][C:39](=[O:46])[C@H:40]([CH2:42][CH:43]([CH3:45])[CH3:44])[NH2:41])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][NH:41][C@@H:40]([CH2:42][CH:43]([CH3:44])[CH3:45])[C:39]([O:38][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[O:46])=[CH:21][CH:22]=2)[C:6](=[O:23])[CH:5]=[CH:4][C:3]=1[C:24](=[O:32])[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 53718217HCID 53718217, compound2×HCID 57658356Methanesulfonic acid 3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxo-2H-pyridin-1-yl]phenoxy}propyl ester

Product 1

HCID 57658385Cyclopentyl(S)-2-(3-{4-[6-Amino-5-(4-fluorobenzoyl)-2-oxo-2H-pyridin-1-yl]phenoxy}propylamino)-4-methylpentanoate

Procedure

From Intermediate 4B and L-leucine cyclopentyl ester (Intermediate 8), LCMS purity 97%, m/z 564 [M+H]+, 1H NMR (400 MHz, d6-DMSO), δ: 0.90 (6H, m), 1.60-1.75 (10H, m), 1.90 (2H, m), 2.15 (2H, m), 3.10-3.30 (2H, m), 4.10 (1H, m), 4.15 (2H, m), 5.30 (1H, m), 5.70 (1H, d). 7.15 (2H, d), 7.30 (2H, d), 7.35 (2H, t), 7.50 (1H, d), 7.55 (1H, m) 9.05-30 (2H, m).

Sources & evidence

ORD record
ord-7d9acd56f614489e8d527cd7019d6c8f
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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