Propionic Acid → HCID 21948181, compound

HRID 1839388Notes

Reaction equation

HRID 1839388 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:9]=[C:8]2[C:3]=1[C:4](=[O:31])[CH:5]=[C:6]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[N:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:32](O)(=[O:35])[CH2:33][CH3:34].CCN=C=NCCCN(C)C.CN1CCOCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:14][CH2:13]2)[N:9]=[C:8]2[C:3]=1[C:4](=[O:31])[CH:5]=[C:6]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[N:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 1032Propionic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10223346HCID 10223346, compound

Product 1

HCID 21948181HCID 21948181, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methyl-1-phenyl-2-phenylamino-7-piperazin-1-yl-1H-[1,8]naphthyridin-4-one (21.0 mg, 0.052 mmol), propionic acid (0.004 mL, 0.055 mmol), EDCI (11.9 mg, 0.062 mmol), DMAP (7.6 mg, 0.062 mmol), and NMM (0.006 mL, 0.062) in CH2Cl2 (0.8 mL) was stirred at room temperature overnight. The reaction was diluted with water and extracted with CH2Cl2. The combined organic extracts were washed with 0.5 N HCl and brine and concentrated in vacuo. The residue was purified by prep-TLC eluting with 100% EtOAc to give 5-methyl-1-phenyl-2-phenylamino-7-(4-propionyl-piperazin-1-yl)-1H-[1,8]naphthyridin-4-one (9.0 mg, 37%): LCMS RT: 2.29 min, MH+: 468.3.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic extracts were washed with 0.5 N HCl and brine
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washby prep-TLC eluting with 100% EtOAc

Sources & evidence

ORD record
ord-6d877f0ab9e44047b12b2885d3dabe1a
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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