5-Methoxybenzofuran-2-carboxylic acid → 5-methoxy-N-(5-methylhexan-3-yl)benzofuran-2-carboxamide

HRID 1644041Notes

Reaction equation

HRID 1644041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[CH:8][C:7]=2[CH:14]=1.[CH3:15][CH:16]([CH3:22])[CH2:17][CH:18]([NH2:21])[CH2:19][CH3:20]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:21][CH:18]([CH2:17][CH:16]([CH3:22])[CH3:15])[CH2:19][CH3:20])=[O:13])=[CH:8][C:7]=2[CH:14]=1

Participants

3

Reactant 2

HCID 2886385-Methoxybenzofuran-2-carboxylic acidHCID 229554965-Methylhexan-3-amine

Product 1

HCID 575277735-methoxy-N-(5-methylhexan-3-yl)benzofuran-2-carboxamideYield 67%

Procedure

Prepared in a similar manner to example 4 using 5-methoxybenzofuran-2-carboxylic acid and 5-methylhexan-3-amine (example 5a). Yield: 67%. 1H NMR (500 MHz, CDCl3): δ 0.96 (m, 9H); 1.39-1.52 (m, 3H); 1.66 (m, 2H); 3.85 (s, 3H); 4.17 (m, 1H); 6.24 (d, 1H); 7.01 (dd, 1H); 7.08 (d, 1H); 7.38 (m, 2H). MS (290, M+H).

Sources & evidence

ORD record
ord-1d8ce9bb29be4f04aca5184aa9ce83ac
Source dataset
uspto-grants-2012_02
Patent number
US08124121B2

Reaction notes

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