Hydrochloric Acid → 2-[(4-Chloro-phenyl)-(1-methyl-6-oxo-piperidin-3-ylamino)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204325Notes

Reaction equation

HRID 2204325 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:7]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)O)=[O:5])[CH3:2].[NH2:23][CH:24]1[CH2:29][N:28]([CH3:30])[C:27](=[O:31])[CH2:26][CH2:25]1.Cl.COC(C1C=C(Br)N(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O.ClC1C=C(C=CC=1F)N>>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:7]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[NH:23][CH:24]1[CH2:25][CH2:26][C:27](=[O:31])[N:28]([CH3:30])[CH2:29]1)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 97083-Chloro-4-fluoroanilineHCID 510721765-Amino-1-methylpiperidin-2-oneHCID 867031015-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 867031332-[(4-Chloro-phenyl)-(1-methyl-6-oxo-piperidin-3-ylamino)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Step D2, but 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step E4) and 5-amino-1-methylpiperidin-2-one [1228838-10-5] (free base was made from the purchased HCl salt) were used instead of 5-bromo-2-[(4-chloro-phenyl)hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 3-chloro-4-fluoroaniline respectively to afford the title compound (diastereomeric mixture) as an off-white solid. tR: 4.31 min (HPLC 1); ESI-MS: tR=1.13/1.15 min, [M+H]+ 432/434 (LC-MS 1); TLC: Rf=0.25 (EtOAc).

Workup

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

Sources & evidence

ORD record
ord-7efacea95ccd4eb381302a0313e949d2
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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