1-Hydroxybenzotriazole → HCID 53328220, compound

HRID 1615408Notes

Reaction equation

HRID 1615408 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([OH:10])=O)[CH3:2].C1C=CC2N(O)N=NC=2C=1.[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][NH:29][C:30]([C:32]2[CH:37]=[CH:36][C:35]([N:38]3[CH2:43][CH2:42][CH:41]([NH:44][C:45]([N:47]4[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]4)=[O:46])[CH2:40][CH2:39]3)=[CH:34][CH:33]=2)=[O:31])[CH2:23][CH2:22]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([N:50]1[CH2:51][CH2:52][N:47]([C:45]([NH:44][CH:41]2[CH2:42][CH2:43][N:38]([C:35]3[CH:34]=[CH:33][C:32]([C:30](=[O:31])[NH:29][CH2:28][CH2:27][N:24]4[CH2:23][CH2:22][O:21][CH2:26][CH2:25]4)=[CH:37][CH:36]=3)[CH2:39][CH2:40]2)=[O:46])[CH2:48][CH2:49]1)=[O:10])[CH3:2]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 154425984778-76-1HCID 71073992HCID 71073992, compound

Product 1

HCID 53328220HCID 53328220, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-ethylpyrrole-2-carboxylic acid (139 mg, 1.0 mmol) was dissolved in DMF (3.0 ml), and WSCD (230 mg, 1.2 mmol), HOBt (168 mg, 1.2 mmol), and N-(1-(4-(2-morpholinoethylcarbamoyl)phenyl)-piperidin-4-yl)-1-piperazinecarboxamide (400 mg, 0.9 mmol) obtained in Example 15(5) was added thereto, followed by stirring under heat at 80° C. for 14 hours. After the reaction mixture was allowed to cool to room temperature, a saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with chloroform. The extract was washed with water and saturated sodium chloride, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium-pressure silica gel flash column chromatography (methanol:chloroform=1:30 to 1:10), thereby obtaining 4-((1-ethylpyrrol-2-yl)-carbonyl)-N-(1-(4-(2-morpholinoethylcarbamoyl)phenyl)-piperidin-4-yl)-1-piperazinecarboxamide (213 mg, 42%) as a milky-white solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with chloroform
  3. washThe extract was washed with water and saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified

Sources & evidence

ORD record
ord-72ea613b511f485caab8b62168f6b770
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

Loading…