Benzenemethanamine, 3,4-dichloro- → HCID 54723976, compound

HRID 1453861Notes

Reaction equation

HRID 1453861 reaction equation
[OH:1][C:2]1[C:3]([C:21]([O:23]C)=O)=[N:4][N:5]2[CH2:10][CH2:9][N:8]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])[C:7](=[O:20])[C:6]=12.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:29][NH2:30]>>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:29][NH:30][C:21]([C:3]1[C:2]([OH:1])=[C:6]2[C:7](=[O:20])[N:8]([CH2:11][C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])[CH2:9][CH2:10][N:5]2[N:4]=1)=[O:23]

Participants

3

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 68895022HCID 68895022, compound

Product 1

HCID 54723976HCID 54723976, compound

Conditions

Temperature
90 °C

Procedure

Methyl 3-hydroxy-5-[(2-morpholin-4-yl)-2-oxoethyl]-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (15 mg, 0.044 mmol) was dissolved in 3,4-dichlorobenzylamine (1.5 mL) and heated to 90° C. for 30 minutes. Purification by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions afforded the title product. 1H NMR (400 MHz, d6-DMSO) δ 8.89-8.86 (t, 1H), 7.55-7.51 (m, 2H), 7.27-7.25 (d, 1H), 4.40-4.38 (d, 2H), 4.33-4.29 (m, 4H), 3.84 (br s, 1H), 3.74-3.71 (t, 2H), 3.58-3.52 (m, 4H), 3.42-3.39 (m, 4H); ES MS (M+1)=482.

Workup

  1. customPurification by reverse phase chromatography on a C-18 column
  2. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-87d50edb2e75413ebdcbe5f2ae0ed73c
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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