Acetic Acid → HCID 70872397, compound

HRID 1616448Notes

Reaction equation

HRID 1616448 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][CH:31]=2)[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:19]=1[CH3:20])=[O:13].[C:43](O)(=[O:45])[CH3:44].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.CO.C(Cl)Cl.O>[C:43]([N:25]1[CH2:24][CH2:23][CH:22]([N:21]([CH2:28][CH3:29])[C:18]2[C:19]([CH3:20])=[C:14]([C:12]([NH:11][CH2:10][C:3]3[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])=[O:13])[CH:15]=[C:16]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][N:37]4[CH2:38][CH2:39][O:40][CH2:41][CH2:42]4)=[CH:32][CH:31]=3)[CH:17]=2)[CH2:27][CH2:26]1)(=[O:45])[CH3:44]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 70872340HCID 70872340, compound

Product 1

HCID 70872397HCID 70872397, compoundYield 37.31%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(piperidin-4-yl)amino)-4-methyl-4′-(morpholinomethyl)-[1,1′-biphenyl]-3-carboxamide (0.25 g, 0.44 mmol) and acetic acid (0.052 g, 0.86 mmol) in DMF (3 mL), EDCI (0.123 g, 0.64 mmol) and HOBt (0.087 g, 0.64 mmol) was added followed by the addition of triethylamine (0.108 g, 1.06 mmol) and reaction was stirred at room temperature for overnight. After completion of the reaction, water was added to it and extraction was carried out using 10% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to give the title compound (0.1 g, 37.31%).

Workup

  1. additionwas added to it and extraction
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude material which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-32ec51dab92f4e7197bde5c1fbc96f4e
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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