Morpholine → HCID 86711842, compound

HRID 623758Notes

Reaction equation

HRID 623758 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:16])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 86711841HCID 86711841, compound

Product 1

HCID 86711842HCID 86711842, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylic acid (1.71 g, 7.26 mmol) and DIPEA (1.39 mL, 7.98 mmol) in DCM (50 mL) were added morpholine (664 μL, 7.62 mmol), HOAt (99 mg, 726 μmol) and EDCI (1.53 g, 7.98 mmol) and the reaction mixture was stirred at room temperature for 2 h. The mixture was washed with brine (100 mL) and the organic layer was dried (Na2SO4) and concentrated. Purification by column chromatography (silica, DCM/(7 M NH3 in MeOH), 98:2) afforded the desired product (1.73 g, 78%).

Workup

  1. washThe mixture was washed with brine (100 mL)
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by column chromatography (silica, DCM/(7 M NH3 in MeOH), 98:2)

Sources & evidence

ORD record
ord-3c889c9f2f2244689f2e844f842ab00f
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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