Acetic Acid → HCID 178474997, compound

HRID 2208778Notes

Reaction equation

HRID 2208778 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]([CH3:30])[C:9]2[C:10]([CH3:29])=[C:11]([CH:25]=[C:26]([Br:28])[CH:27]=2)[C:12]([NH:14][CH2:15][C:16]2[C:17](=[O:24])[NH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])=[O:13])[CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[C:60](O)(=[O:62])[CH3:61]>CN(C=O)C.O>[C:60]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]([CH3:30])[C:9]2[C:10]([CH3:29])=[C:11]([CH:25]=[C:26]([Br:28])[CH:27]=2)[C:12]([NH:14][CH2:15][C:16]2[C:17](=[O:24])[NH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])=[O:13])[CH2:6][CH2:7]1)(=[O:62])[CH3:61]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178425134HCID 178425134, compound

Product 1

HCID 178474997HCID 178474997, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of trans-3-((4-aminocyclohexyl)(methyl)amino)-5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methylbenzamide (0.225, 0.474 mmol) in DMF (3 mL), EDCI.HCl (0.138 g, 0.718 mmol), HOBt (0.064 g, 0.47 mmol), triethyl amine (0.1 g, 0.99 mmol) and acetic acid (0.057 g, 0.949 mmol) were added at room temperature and stirred at same temperature for 18 h. On completion, water was added and extracted with 10% MeOH/DCM. Combined organic layers were dried, concentrated giving crude material; which then purified by column chromatography to afford desired compound (0.13 g, 53%).

Workup

  1. extractionextracted with 10% MeOH/DCM
  2. customCombined organic layers were dried
  3. concentrationconcentrated
  4. customgiving crude material
  5. customwhich then purified by column chromatography

Sources & evidence

ORD record
ord-28ab75d7b92547c6b82cd39ea995165b
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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