Veratric Acid → HCID 68683725, compound

HRID 1992752Notes

Reaction equation

HRID 1992752 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.S(Cl)(Cl)=O.C(OC([N:25]1[CH2:29][CH2:28][CH:27]([NH:30][CH2:31][C:32]([CH3:42])=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[F:41])[CH2:26]1)=O)(C)(C)C>C(N(CC)CC)C>[F:41][C:35]1[CH:36]=[C:37]([F:40])[CH:38]=[CH:39][C:34]=1[CH:33]=[C:32]([CH3:42])[CH2:31][N:30]([CH:27]1[CH2:28][CH2:29][NH:25][CH2:26]1)[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 7121Veratric AcidHCID 24386Thionyl ChlorideHCID 68680927HCID 68680927, compound

Product 1

HCID 68683725HCID 68683725, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Experimental condition analogous to Example 18 were used with 3,4-dimethoxybenzoic acid 0.12 g (0.68 mmol), thionyl chloride 2 ml (1.68 mmol). The obtained acyl chloride was reacted with 3-[3-(2,4-difluoro-phenyl)-2-methyl-allylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester 0.2 g (0.56 mmol), triethylamine 0.2 ml. The reaction yielded the free amine, which was converted to the HCl salt 90 mg as an off-white solid: Yield: 35%.

Sources & evidence

ORD record
ord-3251d86cb86d4f12bf2da72f5c75d361
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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