Piperidine → 3-Amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

HRID 1404540Notes

Reaction equation

HRID 1404540 reaction equation
C1C2C(COC(=O)[NH:17][C:18]3([C:22](=[O:47])[NH:23][C@@H:24]([C:26]4[C:31]([F:32])=[CH:30][C:29]([C:33]5[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([F:40])[C:34]=5[C:41]5[N:45]=[C:44]([CH3:46])[O:43][N:42]=5)=[CH:28][N:27]=4)[CH3:25])[CH2:21][O:20][CH2:19]3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)Cl>[Cl:39][C:37]1[CH:36]=[C:35]([F:40])[C:34]([C:41]2[N:45]=[C:44]([CH3:46])[O:43][N:42]=2)=[C:33]([C:29]2[CH:30]=[C:31]([F:32])[C:26]([C@H:24]([NH:23][C:22]([C:18]3([NH2:17])[CH2:21][O:20][CH2:19]3)=[O:47])[CH3:25])=[N:27][CH:28]=2)[CH:38]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 67979324[3-((R)-1-{5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylcarbamoyl)-oxetan-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 679794613-Amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylcarbamoyl)-oxetan-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester (71.9 mg, 0.107 mmol, step C) in DCM (5 ml) was added piperidine (0.5 ml) and the mixture was stirred at room temperature for 1 h. The colorless solution was concentrated to dryness under high vacuum. The remaining residue was purified by chromatography (silica gel; DCM/MeOH 98:2-95:5) and the title compound was obtained as colorless gum (36 mg, 75%). MS: 450.2 [M+H]+.

Workup

  1. concentrationThe colorless solution was concentrated to dryness under high vacuum
  2. customThe remaining residue was purified by chromatography (silica gel; DCM/MeOH 98:2-95:5)

Sources & evidence

ORD record
ord-7651818ac4b245e2a68aa966b76ba569
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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