Nicotinic Acid → HCID 25066340, compound

HRID 1958762Notes

Reaction equation

HRID 1958762 reaction equation
C1C=NC=C(C(O)=O)C=1.Br[C:11]1[O:15][C:14]([C:16]([NH:18][C@@H:19]([CH2:24][N+:25]([CH3:28])([CH3:27])[CH3:26])[CH2:20][C:21]([O-:23])=[O:22])=[O:17])=[CH:13][CH:12]=1.[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:32]=1)#[CH:30]>>[CH2:38]([O:37][C:33]1[CH:32]=[C:31]([C:29]#[C:30][C:11]2[O:15][C:14]([C:16]([NH:18][C@@H:19]([CH2:24][N+:25]([CH3:28])([CH3:27])[CH3:26])[CH2:20][C:21]([O-:23])=[O:22])=[O:17])=[CH:13][CH:12]=2)[CH:36]=[CH:35][CH:34]=1)[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

4

Reactant 3

HCID 938Nicotinic AcidHCID 25066535HCID 25066535, compoundHCID 86641235HCID 86641235, compound

Product 1

HCID 25066340HCID 25066340, compoundYield 20%

Procedure

According to the method described in example S115, (R)-3-(5-bromofuran-2-carboxamido)-4-(trimethylammonio)butanoate was reacted with 1-ethynyl-3-(hexyloxy)benzene. The crude product was purified by silica gel chromatography (CH2Cl2/MeOH 3:2) to give the title compound as a white powder (11.1 mg, 20%). 1H NMR (400 MHz, D2O) δ 6.94-6.89 (m, 2H), 6.81-6.79 (m, 1H), 6.57 (s, 1H), 6.46-6.44 (m, 1H), 6.30 (s, 1H), 4.80-4.76 (m, 1H), 3.67-3.45 (m, 4H), 3.01 (s, 9H), 2.44-2.35 (m, 2H), 1.38-1.32 (m, 2H), 1.10-0.95 (m, 6H), 0.61 (t, 3H, J=6.4 Hz); MS ESI [M+H]+, calcd for [C26H34N2O5+H]+ 455.25; found m/z 455.3.

Workup

  1. customThe crude product was purified by silica gel chromatography (CH2Cl2/MeOH 3:2)

Sources & evidence

ORD record
ord-207ded056e0f482c96b85eb633ed367f
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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