HCID 57658359, compound → Cyclopentyl N-(3-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}propyl)-D-leucinate

HRID 1667375Notes

Reaction equation

HRID 1667375 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[C:22]([F:23])=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][C:9]=2[F:24])[C:6](=[O:25])[CH:5]=[CH:4][C:3]=1[C:26](=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34].[CH:36]1([O:41][C:42](=[O:49])[C@@H:43]([CH2:45][CH:46]([CH3:48])[CH3:47])[NH2:44])[CH2:40][CH2:39][CH2:38][CH2:37]1>>[NH2:1][C:2]1[N:7]([C:8]2[C:22]([F:23])=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15][NH:44][C@@H:43]([C:42]([O:41][CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)=[O:49])[CH2:45][CH:46]([CH3:47])[CH3:48])=[CH:10][C:9]=2[F:24])[C:6](=[O:25])[CH:5]=[CH:4][C:3]=1[C:26](=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34]

Participants

3

Reactant 2

HCID 57658359HCID 57658359, compoundHCID 59139924HCID 59139924, compound

Product 1

HCID 57658368Cyclopentyl N-(3-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}propyl)-D-leucinate

Procedure

From Intermediate 4F and D-Leucine cyclopentyl ester, LCMS purity 95%, m/z 618 [M+H]+, 1H NMR (300 MHz, DMSO), δ: 10.10 (1H, brs), 9.40-9.10 (2H, m), 8.15 (1H, br s), 7.62-7.52 (1H, m), 7.47-7.31 (2H, m), 7.28-7.12 (1H, m), 7.07 (2H, d, J=10.5 Hz), 5.73 (1H, d, J=9.6 Hz), 5.30-5.20 (1H, m), 4.25-4.00 (3H, m), 3.30-3.00 (2H, m), 2.20-2.00 (2H, m), 1.95-1.80 (2H, m), 1.75-1.55 (10H, m), 1.00-0.90 (6H, m).

Sources & evidence

ORD record
ord-46a517116d414be4b1678e8132a11852
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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