Pivalic acid → HCID 70872236, compound

HRID 1530290Notes

Reaction equation

HRID 1530290 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]=[C:34](CN3CCOCC3)[CH:33]=[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]([OH:49])(=O)[C:44]([CH3:47])([CH3:46])[CH3:45].[CH2:50]([N:52]([CH2:55][CH3:56])[CH2:53]C)[CH3:51].C1CN([P+]([O:73]N2N=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]([CH2:53][N:52]3[CH2:55][CH2:56][O:73][CH2:51][CH2:50]3)=[CH:32][CH:31]=2)[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]2[CH2:27][CH2:26][N:25]([C:43](=[O:49])[C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:24][CH2:23]2)[C:19]=1[CH3:20])=[O:13]

Participants

6

Reactant 4

HCID 6417Pivalic acidHCID 8471TriethylamineHCID 2724699PyBOPHCID 131733226HCID 131733226, 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)-[1,2′-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-32e1baa3a26c471883ef7ca883fabd9f
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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