Dimethylamine → HCID 17838209, compound

HRID 1352146Notes

Reaction equation

HRID 1352146 reaction equation
[CH3:1][NH:2][CH3:3].[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][CH:14]3[CH2:19][CH2:18][CH2:17][N:16]([CH:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:21]([OH:23])=O)[CH2:15]3)=[CH:10][CH:11]=2)[CH:6]=[N:5]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.CN(C1C=CC=CN=1)C>[CH3:1][N:2]([CH3:3])[C:21](=[O:23])[CH:20]([N:16]1[CH2:17][CH2:18][CH2:19][CH:14]([NH:13][C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[NH:4][N:5]=[CH:6]3)[CH2:15]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17838237HCID 17838237, compound

Product 1

HCID 17838209HCID 17838209, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Dimethylamine (100 mg) and the compound prepared in Example 222 (350 mg) were dissolved in dimethylformamide (5 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (257 mg), 1-hydroxybenzotriazole (227 mg), and dimethylaminopyridine (5 mg) were added to the solution. The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (5 ml) was then added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC [chloroform/methanol]t to give 180 mg of the title compound as two diastereomers (ratio=ca. 50:50)).

Workup

  1. extractionthe mixture was extracted with chloroform-propanol (3/1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by HPLC [chloroform/methanol]t

Sources & evidence

ORD record
ord-100b8aac786d4193a5e8411f4ee42cf2
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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