1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Methyl 5-{[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl}-2-fluorobenzoate

HRID 551981Notes

Reaction equation

HRID 551981 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([OH:9])=O.CCN=C=NCCCN(C)C.Cl.[CH2:27]([C:31]1[CH:36]=[CH:35][C:34]([C:37]#[C:38][C:39]2[CH:52]=[CH:51][C:42]([CH2:43][NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:41][CH:40]=2)=[CH:33][CH:32]=1)[CH2:28][CH2:29][CH3:30]>>[CH2:27]([C:31]1[CH:36]=[CH:35][C:34]([C:37]#[C:38][C:39]2[CH:52]=[CH:51][C:42]([CH2:43][N:44]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:7]([C:6]3[CH:10]=[CH:11][C:12]([F:13])=[C:4]([CH:5]=3)[C:3]([O:2][CH3:1])=[O:14])=[O:9])=[CH:41][CH:40]=2)=[CH:33][CH:32]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57554478N-{4-[(4-butylphenyl)ethynyl]benzyl)-1-hexanamineHCID 575544904-Fluoro-3-(methoxycarbonyl)benzoic acid

Product 1

HCID 57554508Methyl 5-{[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl}-2-fluorobenzoateYield 74%

Procedure

The title compound was prepared following procedure described in Example 19, step c) from 4-fluoro-isophtalic acid-3-methylester (199 mg; 1.01 mmol), EDC.HCl (212 mg; 1.11 mmol) and N-{4-[(4-butylphenyl)ethynyl]benzyl}-1-hexanamine (350 mg, 1.01 mmol). Purification of the crude (503 mg) by flash chromatography using silicagel (EtOAc/c-Hex, 20:80) afforded 394 mg (74%) of the title compound as a colorless oil. HPLC, Rt: 6.19 min (purity: 99.8%), LC/MS, M+(ESI): 528.4.1HN (CDCl3) δ: 7.99 (d, J=5.1 Hz, 1H), 7.98 (m, 1H), 7.49 (d, J=8.1 Hz, 2H), 7.42 (d, J=8.1 Hz, 2H), 7.31 (m, 1H), 7.15 (d, J=8.1 Hz, 4H), 4.73 (s, 1H), 4.48 (s, 1H), 3.91 (s, 3H), 3.44 (s, 1H), 3.11 (s, 1H), 2.60 (t, J=7.6 Hz, 2H), 1.35 (m, 4H), 1.08-1.37 (m, 8H), 0.90 (t, J=7.3 Hz, 3H), 0.83 (m, 3H).

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification of the crude (503 mg) by flash chromatography

Sources & evidence

ORD record
ord-5aee67b71ee5435da9c6fc500ff76f32
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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