Dimethylamine, hydrochloride → HCID 178484624, compound

HRID 2423248Notes

Reaction equation

HRID 2423248 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[F:27][C:28]1[CH:29]=[C:30]([C:35](=[O:63])[C:36](=[C:54]2[NH:58][C:57]3[CH:59]=[CH:60][CH:61]=[CH:62][C:56]=3[NH:55]2)[C:37]([C:39]2[CH:40]=[C:41]([S:45]([NH:48][C:49](=[NH:53])[C:50]([OH:52])=O)(=[O:47])=[O:46])[CH:42]=[CH:43][CH:44]=2)=[O:38])[CH:31]=[C:32]([F:34])[CH:33]=1>O.CN(C=O)C.C(N(CC)CC)C>[F:34][C:32]1[CH:31]=[C:30]([C:35](=[O:63])[C:36](=[C:54]2[NH:58][C:57]3[CH:59]=[CH:60][CH:61]=[CH:62][C:56]=3[NH:55]2)[C:37]([C:39]2[CH:40]=[C:41]([S:45]([NH:48][C:49](=[NH:53])[C:50]([N:3]([CH3:4])[CH3:2])=[O:52])(=[O:46])=[O:47])[CH:42]=[CH:43][CH:44]=2)=[O:38])[CH:29]=[C:28]([F:27])[CH:33]=1

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178513453HCID 178513453, compound

Product 1

HCID 178484624HCID 178484624, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Dimethylamine hydrochloride (31 mg), triethylamine (0.05 mL), HOBt (51 mg) and WSC.HCl (73 mg) were added to a DMF (5 mL) solution of [({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)amino](imino)acetic acid (40 mg), followed by stirring at room temperature for 1.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to obtain 2-[({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)amino]-2-imino-N,N-dimethylacetamide (28 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-4ecd2acb362a47e28f5df73e1c90ef63
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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