Dimethylamine, hydrochloride → HCID 23130301, compound

HRID 2114166Notes

Reaction equation

HRID 2114166 reaction equation
Cl.[NH2:2][C:3]1[C:8]([C:9](O)=[O:10])=[C:7]([F:12])[C:6]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([F:21])[CH:4]=1.Cl.[CH3:23][NH:24][CH3:25].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[NH2:2][C:3]1[C:8]([C:9]([N:24]([CH3:25])[CH3:23])=[O:10])=[C:7]([F:12])[C:6]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([F:21])[CH:4]=1

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86035991HCID 86035991, compound

Product 1

HCID 23130301HCID 23130301, compoundYield 59.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-amino-3-benzyloxy-2,4-difluorobenzenecarboxylic acid hydrochloride (2.07 g) in DMF (30 mL) were added dimethylamine hydrochloride (1.07 g), 1-hydroxybenzotriazole (1.51 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.89 g) and triethylamine (2.0 g), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, washed successively with water, saturated aqueous sodium bicarbonate, water and brine, dried over sodium sulfate and purified by column chromatography (hexane:ethyl acetate=1:2) on silica gel to give 6-amino-3-benzyloxy-2,4-difluoro-N,N-dimethylbenzamide (1.19 g).

Workup

  1. washwashed successively with water, saturated aqueous sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate
  3. custompurified by column chromatography (hexane:ethyl acetate=1:2) on silica gel

Sources & evidence

ORD record
ord-b214a1cfac4a4fb09eb5a1597fb4a1a6
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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