Hydrochloric Acid → HCID 69242553, compound

HRID 1594186Notes

Reaction equation

HRID 1594186 reaction equation
ClC1C=CC(CN[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([N:24]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30](Cl)=[CH:29][C:28]=2Cl)=[O:23])=[O:9])=CC=1.[N:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][NH2:49])[CH:43]=1.Cl.[CH2:51](N=C=NCCCN(C)C)[CH3:52].Cl.[C:63](OCC)(=[O:65])[CH3:64]>C(Cl)Cl>[CH2:51]([O:39][C:37](=[O:38])[CH2:36][CH2:35][N:24]([C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]([NH:49][CH2:48][C:44]1[CH:43]=[N:42][CH:47]=[CH:46][CH:45]=1)=[O:9])=[O:23])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:65][CH2:63][CH3:64])=[CH:31][CH:32]=1)[CH3:52]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 310183-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23079124HCID 23079124, compound

Product 1

HCID 69242553HCID 69242553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound prepared in reference example 2 (150 mg), 3-picolylamine (50 mg) and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (180 mg) were dissolved in methylene chloride (5 ml) and the mixture was stirred overnight at room temperature. The reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid and the aqueous layer was extracted with ethyl acetate. Combined organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=1:2) to give the compound (147 mg) having the following physical data.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washCombined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-47699e3356404bcab8c85450ce6f5ab3
Source dataset
uspto-grants-2007_11
Patent number
US07300917B2

Reaction notes

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