2-Methylbenzofuran-3-carbonyl Chloride → 2-Methyl-benzofuran-3-carboxylic acid butyl-(6-hydroxy-naphthalen-2-ylmethyl)-amide

HRID 1357299Notes

Reaction equation

HRID 1357299 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2)[CH2:2][CH2:3][CH3:4].[CH3:18][C:19]1[O:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]=1[C:24](Cl)=[O:25]>>[CH2:1]([N:5]([CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=2)[CH:8]=1)[C:24]([C:23]1[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[O:20][C:19]=1[CH3:18])=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 185053172-Methylbenzofuran-3-carbonyl ChlorideHCID 185053566-Butylaminomethyl-naphthalen-2-ol

Product 1

HCID 691384262-Methyl-benzofuran-3-carboxylic acid butyl-(6-hydroxy-naphthalen-2-ylmethyl)-amideYield 47%

Procedure

Prepared in the same manner as described in step 4 of Example 48 and replacing 6-(benzylamino-methyl)-naphthalen-2-ol with 6-butylaminomethyl-naphthalen-2-ol, prepared in step 3 of Example 51, and replacing 2-butyl-benzofuran-3-carbonyl chloride with 2-methy-benzofuran-3-carbonyl chloride, prepared in step 2 of Example 20. Purification of the crude product on 300 g silica gel (230-400 mesh) using 25%-33% ethyl acetate in hexane as the eluent gave 2-methyl-benzofuran-3-carboxylic acid butyl-(6-hydroxy-naphthalen-2-ylmethyl)-amide (1.03 g, 47%) as a tan solid, mp 126-128° C.

Workup

  1. customPrepared in the same manner
  2. customprepared in step 3 of Example 51
  3. customprepared in step 2 of Example 20
  4. customPurification of the crude product on 300 g silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-d99677e3b3284b8fad41477fb8e48daf
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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