Colchicine → 2-Methyl-cyclopropanecarboxylic acid (3,9,10,11-tetramethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-5-yl)-amide

HRID 1437859Notes

Reaction equation

HRID 1437859 reaction equation
Cl[C:2]1[C:10](C)=CC=C[C:3]=1C(O)=O.[CH3:12][C:13]([NH:15][C@@H:16]1[C:32]2[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])C([CH:31]=2)=O)[C:24]2[C:23]([O:35][CH3:36])=[C:22]([O:37][CH3:38])[C:21]([O:39][CH3:40])=[CH:20][C:19]=2[CH2:18][CH2:17]1)=[O:14]>>[CH3:34][O:33][C:28]1[CH:27]=[CH:26][C:25]2[C:24]3[C:23]([O:35][CH3:36])=[C:22]([O:37][CH3:38])[C:21]([O:39][CH3:40])=[CH:20][C:19]=3[CH2:18][CH2:17][CH:16]([NH:15][C:13]([CH:12]3[CH2:3][CH:2]3[CH3:10])=[O:14])[C:32]=2[CH:31]=1

Participants

3

Reactant 2

HCID 6167ColchicineHCID 1398792-Chloro-3-methylbenzoic acid

Product 1

HCID 766537982-Methyl-cyclopropanecarboxylic acid (3,9,10,11-tetramethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-5-yl)-amide

Procedure

The same method used in Example 25 was carried out to obtain the title compound 41 (95 mg, Yield: 76%) except that (−)-7-deacetyl-9-methoxy allocolchicine was used instead of (−)-thiodeacetyl colchicine.

Sources & evidence

ORD record
ord-4f8308d572524d96bb6f3cd78b07ed15
Source dataset
uspto-grants-2009_11
Patent number
US07622612B2

Reaction notes

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