4-Methoxyphenylacetic Acid → HCID 59636687, compound

HRID 2098204Notes

Reaction equation

HRID 2098204 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[CH3:13][C:14]1[N:15]=[CH:16][N:17]([C:19]2[S:20][CH:21]=[CH:22][C:23]=2[NH2:24])[CH:18]=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([NH:24][C:23]2[CH:22]=[CH:21][S:20][C:19]=2[N:17]2[CH:18]=[C:14]([CH3:13])[N:15]=[CH:16]2)=[O:12])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 76904-Methoxyphenylacetic AcidHCID 68783599HCID 68783599, compound

Product 1

HCID 59636687HCID 59636687, compoundYield 6%

Procedure

2-(4-methoxyphenyl)-N-(2-(4-methyl-1H-imidazol-1-yl)thiophen-3-yl)acetamide was prepared from 2-(4-methoxyphenyl)acetic acid and 2-(4-methyl-1H-imidazol-1-yl)thiophen-3-amine according to the procedure described in Example 9.7.3., above. Purification by flash column chromatography afforded the final product (silica, 75:25 ethyl acetate/hexane) (77 mg, 6%). Method [7] m/z 328.0 (M+H); retention time=1.001. 1H-NMR (CDCl3) δ 8.00 (broad s, 1H), 7.77 (d, J=6.4 Hz, 1H), 7.16 (s, 1H), 7.13 (d, J=8.7 Hz, 2H), 6.85 (d, J=8.7 Hz, 2H), 6.50 (s, 1H), 3.81 (s, 3H), 3.65 (s, 2H), 2.15 (d, J=0.9 Hz, 2H).

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-1dafe560938141b3b31304b0eb9a486a
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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