3-Fluoroaniline → DPI-3290

HRID 1900259Notes

Reaction equation

HRID 1900259 reaction equation
F[C:2]1C=C(C=CC=1)NC.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].[CH2:18]([N:21]1[C@H:26]([CH3:27])[CH2:25][N:24]([C@H:28]([C:43]2[CH:44]=[C:45]([CH:49]=[CH:50][CH:51]=2)[C:46](Cl)=[O:47])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][Si](C(C)(C)C)(C)C)[CH:30]=2)[C@@H:23]([CH3:52])[CH2:22]1)[CH:19]=[CH2:20]>>[CH2:18]([N:21]1[C@H:26]([CH3:27])[CH2:25][N:24]([C@H:28]([C:43]2[CH:44]=[C:45]([CH:49]=[CH:50][CH:51]=2)[C:46]([N:14]([C:13]2[CH:15]=[CH:16][CH:17]=[C:11]([F:10])[CH:12]=2)[CH3:2])=[O:47])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)[C@@H:23]([CH3:52])[CH2:22]1)[CH:19]=[CH2:20]

Participants

4

Reactant 3

HCID 97423-FluoroanilineHCID 27590113-fluoro-N-methylanilineHCID 111350383-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride

Product 1

HCID 9826770DPI-3290

Procedure

3-Fluoro-N-Methylaniline [NMR (200 MHz, DMSO-d6): δ 2.76 (s, 3H); 3.42 (s, 1H); 6.51-6.92 (m, 3H); 7.28 (dt, J1 =7.3 Hz, J2 =8.0 Hz, 1)], was prepared from 3-fluoroaniline, coupled with 3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert -butyldimethylsilyloxy)benzyl)benzoyl chloride, deprotected and purified by the methods described in Example 10 to give (+)-3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide as a light yellow powder.

Workup

  1. custompurified by the methods

Sources & evidence

ORD record
ord-3685ea79235b4d1488c4a3bce0dc863c
Source dataset
uspto-grants-1996_11
Patent number
US05574159

Reaction notes

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