5-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one → 2-bromo-5-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester

HRID 2204355Notes

Reaction equation

HRID 2204355 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)O)[N:8]([CH:25]([CH3:27])[CH3:26])[C:7]=1[Br:28])=[O:5])[CH3:2].[NH2:29][C:30]1[CH:31]=[C:32]([Cl:38])[C:33](=[O:37])[N:34]([CH3:36])[CH:35]=1.C(OC(C1C=CN(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O)C.NC1C(=O)N(C)C=C(Cl)C=1>>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([CH:16]([NH:29][C:30]2[CH:31]=[C:32]([Cl:38])[C:33](=[O:37])[N:34]([CH3:36])[CH:35]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:8]([CH:25]([CH3:27])[CH3:26])[C:7]=1[Br:28])=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-oneHCID 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867031183-Amino-5-chloro-1-methylpyridin-2(1H)-oneHCID 867031642-bromo-5-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester

Product 1

HCID 867031632-bromo-5-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Step L3 but 2-bromo-5-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester (Step BM2) and 5-amino-3-chloro-1-methyl-1H-pyridin-2-one (Step E5) were used instead of 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester and 3-amino-5-chloro-1-methyl-1H-pyridin-2-one respectively. The title compound was obtained as a blue foam. tR: 1.28 min (HPLC 3); ESI-MS: tR=1.25 min, [M+H]+ 612/614/616 (LC-MS 1); TLC: Rf=0.17 (2:1 EtOAc/heptanes).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-9ae43fe3256d4d959e0994dc1a3ff404
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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