4-Methylmorpholine → HCID 45278720, compound

HRID 339738Notes

Reaction equation

HRID 339738 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][C:4]([C:13]([OH:15])=O)=[C:3]1[CH3:16].Cl.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][NH2:35])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.CO>[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][CH2:34][NH:35][C:13]([C:4]3[CH:5]=[C:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:2]([CH3:1])[C:3]=3[CH3:16])=[O:15])[CH2:30][CH2:31]2)[CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 8529041H-Pyrrole-3-carboxylic acid, 1,2-dimethyl-5-phenyl-HCID 46899437HCID 46899437, compound

Product 1

HCID 45278720HCID 45278720, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the mixture of 1,2-Dimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid (100 mg, 0.46 mmol) and 3-(4-(3-chlorophenyl) piperazin-1-yl)propan-1-amine dihydrochloride (152 mg, 0.46 mmol) in methylene chloride (5 ml) was added EDCI (178 mg, 0.92 mmol), HOBT (130 mg, 0.9 mmol) and NMM (0.3 ml, 1.8 mmol) continuously. After stirring for 1 day at room temperature, MeOH was added to the resulting solution, and filter off. After evaporation under reduced pressure, the residue was purified by reverse phase preparative HPLC to provided title compound (149 mg, 71%) as white solid.

Workup

  1. filtrationfilter off
  2. customAfter evaporation under reduced pressure
  3. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-bec662023f5141fd9823607c32997ef6
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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