Hydrochloric Acid → HCID 66818588, compound

HRID 1755109Notes

Reaction equation

HRID 1755109 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[CH2:35][CH2:36][S:37]([N:40]1[CH2:45][CH2:44][C:43](=[O:46])[CH2:42][CH2:41]1)(=[O:39])=[O:38])[C:29]([OH:31])=O.[CH2:47]([O:50][CH2:51][CH2:52][NH:53][CH3:54])[CH:48]=[CH2:49].C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C.O>[CH2:47]([O:50][CH2:51][CH2:52][N:53]([CH3:54])[C:29](=[O:31])[C:28]1[CH:32]=[CH:33][C:34]([CH2:35][CH2:36][S:37]([N:40]2[CH2:45][CH2:44][C:43](=[O:46])[CH2:42][CH2:41]2)(=[O:39])=[O:38])=[C:26]([CH3:25])[CH:27]=1)[CH:48]=[CH2:49]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58684300HCID 58684300, compoundHCID 66816859HCID 66816859, compound

Product 1

HCID 66818588HCID 66818588, compoundYield 116.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (91 mg, 0.239 mmol) was added to a solution of 3-methyl-4-[2-(4-oxo-piperidine-1-sulfonyl)-ethyl]-benzoic acid (50 mg, 0.154 mmol), (2-allyloxy-ethyl)-methyl-amine (36 mg, 0.312 mmol) and diisopropylethylamine (0.065 ml, 0.384 mmol) in DMF (0.5 ml), and the mixture was stirred at room temperature overnight. Water (12 ml) and 1 N hydrochloric acid (1.5 ml) were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was sequentially washed with 0.1 N hydrochloric acid, water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give N-(2-allyloxy-ethyl)-3,N-dimethyl-4-[2-(4-oxo-piperidine-1-sulfonyl)-ethyl]-benzamide (76 mg, 100%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was sequentially washed with 0.1 N hydrochloric acid, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cf5dd392c67d4435b6e7d16fbc098018
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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