Pivalic acid → HCID 70872236, compound

HRID 1616453Notes

Reaction equation

HRID 1616453 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:48])[C:44]([CH3:47])([CH3:46])[CH3:45].C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CS(C)=O>[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[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:32][CH:31]=2)[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]2[CH2:23][CH2:24][N:25]([C:43](=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:26][CH2:27]2)[C:19]=1[CH3:20])=[O:13]

Participants

6

Reactant 4

HCID 6417Pivalic acidHCID 8471TriethylamineHCID 2724699PyBOPHCID 70872340HCID 70872340, compound

Product 1

HCID 70872236HCID 70872236, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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 (0.2 g, 0.34 mmol) was dissolved in DMSO (2 mL) and pivalic acid (0.107 g, 1.04 mmol) and triethyl amine (0.106 g, 1.04 mmol) was added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (0.27 g, 0.52 mmol) was added to it and stirring was continued for overnight. After completion of the reaction, reaction mixture was poured into ice, extracted with 10% MeOH/DCM. Combined organic layers were dried, concentrated to obtain crude; which then purified by column chromatography to afford the title compound (0.14 g, 60.86%).

Workup

  1. additionwas added to it
  2. customAfter completion of the reaction, reaction mixture
  3. additionwas poured into ice
  4. extractionextracted with 10% MeOH/DCM
  5. customCombined organic layers were dried
  6. concentrationconcentrated
  7. customto obtain crude
  8. customwhich then purified by column chromatography

Sources & evidence

ORD record
ord-6ed9ce8f18894c4fa952a626302bb0b9
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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