2-Fluoroaniline → HCID 21480431, compound

HRID 1490080Notes

Reaction equation

HRID 1490080 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](OC(=O)CC)(=O)[CH2:10][CH3:11].[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]>>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:9][CH2:10][CH3:11].[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:4]([C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[F:1])[CH2:9][CH2:10][CH3:11])=[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

5

Reactant 3

HCID 95842-FluoroanilineHCID 31263Propionic anhydrideHCID 111350383-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride

Product 2

HCID 21480431HCID 21480431, compoundHCID 57238577HCID 57238577, compound

Procedure

2-Fluoro-N-propylaniline [NMR (DMSO-d6, 200 MHz): δ 0.93 (t, J=7.4 Hz, 3H); 1.59 (m, 2H); 3.04 (q, 6.5 Hz, 2H); 5.33 (br m, 1H); 6.47-6.58 (m, 1H); 6.70 (t, J=8.1 Hz, 1H); 6.93-7.05 (m, 2H)] was prepared from 2-fluoroaniline and propionic anhydride, 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-(2-fluorophenyl)-N-propylbenzamide as a white solid. NMR (DMSO-d6, 200 MHz): δ 0.9-1.05 (m, 9H); 1.5 (m, 2H); 1.7 (m, 1H); 2.05 (m, 1H); 2.3 (m, 1H); 2.5 (m, 2H); 2.7 (m, 1H); 2.85 (m, 1H); 3.2 (m, 1H); 3.7 (m, 2 H); 4.8 (br s, 1H); 5.1 (d, J=10 Hz, 1H); 5.2 (d, J=16 Hz, 1H); 5.8 (m, 1H); 6.5 (d, J=8 Hz, 1H); 6.6 (s, 1H); 6.65 (d, J=8 Hz, 1H); 7.0-7.4 (m, 9H); 9.3 (s, 1H). [α]D20 =+1.8° (abs ethanol, c=2.8). Calc. for C32H38FN3 O2HCl 0.25 H2O: C, 69.05; H, 7.15; N, 7.55; Cl, 6.37. Found: C, 68.94; H, 7.19; N, 7.57; Cl, 6.41. Mass spectrum (CI--CH4) m/e: 516 (M+1, 93%), 515 (M, 29%), 362 (26%), 153 (100%).

Workup

  1. custompurified by the methods

Sources & evidence

ORD record
ord-d6a997d07b4f414e9e0cb4dc8003253c
Source dataset
uspto-grants-1997_10
Patent number
US05681830

Reaction notes

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