3-Fluoroaniline → HCID 18354680, compound

HRID 741645Notes

Reaction equation

HRID 741645 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[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:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][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:5]([C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=2)[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 97423-FluoroanilineHCID 31263Propionic anhydrideHCID 111350383-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride

Product 2

HCID 18354680HCID 18354680, compoundHCID 56979949HCID 56979949, compound

Procedure

3-Fluoro-N-propylaniline [NMR (DMSO-d6, 200 MHz): δ0.96 (t, J=7.3 Hz, 3H); 1.56 (m, 2H); 2.97 (q, 6.9 Hz, 2H); 5.93 (br m, 1H); 6.22-6.43 (m, 3H); 7.06 (q, J=7.8 Hz, 1H)] was prepared from 3-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-(3-fluorophenyl)-N-propylbenzamide as a light beige solid. NMR (DMSO-d6, 200 MHz): δ0.9-1.05 (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); 3.8 (m, 2H); 4.8 (s, 1H); 5.1 (d, J=10 Hz, 1H); 5.2 (d, J=16 Hz, 1H); 5.8 (m, 1H); 6.45 (d, J=8 Hz, 1H); 6.6 (s, 1H); 6.7 (d, J=8 Hz, 1H); 6.9 (d, J=8 Hz, 1H); 7.0-7.4 (m, 9H); 9.3 (s, 1H). [α]D20 =+4.3° (abs ethanol. c=1.5). Calc. for C32H38FN3O2HCl 0.75 H2O: C, 67.95; H, 7.22; N, 7.43; Cl, 6.27. Found: C, 67.72; H, 7.19; N, 7.49; Cl, 6.30. Mass spectrum (CI--CH4) m/e: 516 (M+1, 100%), 515 (M, 22%), 362 (30%), 153 (73%).

Workup

  1. custompurified by the methods

Sources & evidence

ORD record
ord-ce864f2db96f4e4195ae1b3ac32b9dd3
Source dataset
uspto-grants-1996_09
Patent number
US05552404

Reaction notes

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