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

HRID 2046598Notes

Reaction equation

HRID 2046598 reaction equation
C1C2C(COC(=O)[NH:17][C:18]3([C:22](=[O:47])[NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][C:29]([C:33]6[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([F:40])[C:34]=6[C:41]6[N:45]=[C:44]([CH3:46])[O:43][N:42]=6)=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[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:28]=[C:27]3[C:32](=[CH:31][CH:30]=2)[C@@H:24]([NH:23][C:22]([C:18]2([NH2:17])[CH2:19][O:20][CH2:21]2)=[O:47])[CH2:25][CH2:26]3)[CH:38]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68296802(3-{(S)-5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 601410403-Amino-oxetane-3-carboxylic acid {(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester (intermediate A-12) (2.94 g, 4.42 mmol) in MeCl2 (50.0 ml) was added piperidine (4.38 ml) and the mixture was stirred at room temperature for 15 h. The colorless solution was concentrated to dryness under high vacuum at RT. The remaining residue was purified by chromatography (silica gel; MeCl2/MeOH 100:0-95:5) and the title compound was obtained as light brown oil (1.09 g, 56%). MS: 443.1 (MH+, 1Cl).

Workup

  1. concentrationThe colorless solution was concentrated to dryness under high vacuum at RT
  2. customThe remaining residue was purified by chromatography (silica gel; MeCl2/MeOH 100:0-95:5)

Sources & evidence

ORD record
ord-fe591d7b037b415197032ccb6fc07c31
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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