Hydrochloric Acid → HCID 68681161, compound

HRID 1992750Notes

Reaction equation

HRID 1992750 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][CH2:15][C:16]([CH3:26])=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[CH2:9]1)=O)(C)(C)C.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[C:32](O)=[O:33].S(Cl)(Cl)=O.Cl>O1CCOCC1.C(N(CC)CC)C>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[CH:17]=[C:16]([CH3:26])[CH2:15][N:14]([CH:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[C:32](=[O:33])[C:31]1[CH:30]=[C:29]([O:28][CH3:27])[C:37]([O:38][CH3:39])=[C:36]([O:40][CH3:41])[CH:35]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 83573,4,5-Trimethoxybenzoic AcidHCID 24386Thionyl ChlorideHCID 68681463HCID 68681463, compound

Product 1

HCID 68681161HCID 68681161, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

Experimental condition analogous to Example 18 were used with 3-[3-(2,4-difluoro-phenyl)-2-methyl-allylamino]-piperidine-1-carboxylic acid tert-butyl ester 0.35 g (0.94 mmol), 3,4,5-trimethoxy benzoic acid 0.24 g (1.13 mmol), thionyl chloride 0.15 g (0.94 mmol) and triethylamine 0.1 ml. The reaction yielded 380 mg BOC protected intermediate. This intermediate 0.36 g (0.64 mmol) was dissolved in 5 ml dioxane, 6 N HCl was added, and the mixture was stirred at room temperature for 14 hr. A basic work up led to 319 mg of free amine. This was converted to the HCl salt, yielding 100 mg of a yellow solid. Yield: 33%.

Workup

  1. customThe reaction yielded 380 mg BOC protected intermediate

Sources & evidence

ORD record
ord-8a3e16e494c244f299725aa1c0a9e34b
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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