Methylamine → HCID 17838151, compound

HRID 1352141Notes

Reaction equation

HRID 1352141 reaction equation
CN.[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:20](O)=[O:21])[CH2:14]3)=[CH:9][CH:10]=2)[CH:5]=[N:4]1.Cl.[CH2:30]([N:32]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:30][NH:32][C:20](=[O:21])[CH:19]([N:15]1[CH2:16][CH2:17][CH2:18][CH:13]([NH:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[NH:3][N:4]=[CH:5]3)[CH2:14]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 6

HCID 6329MethylamineHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17838237HCID 17838237, compound

Product 1

HCID 17838151HCID 17838151, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylamine (30 mg) and the compound prepared in Example 222 (88 mg) were dissolved in dimethylformamide (1 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (86 mg), 1-hydroxybenzotriazole (77 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 (1 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] to give 52 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]

Sources & evidence

ORD record
ord-89b2f044a552440e8b5d9f4f30c79384
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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