Pyridine → HCID 70976209, compound

HRID 535630Notes

Reaction equation

HRID 535630 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[NH2:20][N:21]1[N:30]=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:42].N1C=CC=CC=1>ClCCl.CN(C=O)C>[C:40]([C:37]1[CH:38]=[CH:39][C:34]([S:31]([C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:42])[N:21]([NH:20][C:4](=[O:6])[CH2:3][C:2]([CH3:1])([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:7])[N:30]=2)(=[O:33])=[O:32])=[CH:35][CH:36]=1)#[N:41]

Participants

7

Reactant 4

HCID 1049PyridineHCID 13890beta-Phenylisovaleric acidHCID 65578Oxalyl chlorideHCID 70976118HCID 70976118, compound

Product 1

HCID 70976209HCID 70976209, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-3-phenyl butanoic acid (37.7 mg, 0.212 mmol) and oxalyl chloride (0.024 mL, 0.275 mmol) in dichloromethane (0.80 mL) with a drop of DMF was stirred at room temperature for 90 minutes, concentrated to dryness, and re-dissolved in DCM (0.80 mL). To this solution was added the product from Example 224A (60.6 mg, 0.186 mmol) and pyridine (0.020 mL, 0.248 mmol), and the mixture was stirred at room temperature for 2 hours, concentrated, and chromatographed (2% acetone/DCM) to afford 46.4 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.55 (s, 1H), 8.55 (d, J=8.1 Hz, 1H), 8.41 (d, J=7.4 Hz, 1H), 8.16-8.23 (m, 4H), 8.11-8.17 (m, 1H), 8.04 (t, J=7.6 Hz, 1H), 7.40 (d, J=1.7 Hz, 1H), 7.37-7.38 (m, 1H), 7.28-7.34 (m, 2H), 7.19 (t, J=7.2 Hz, 1H), 2.50-2.56 (m, 2H), 1.29 (s, 6H); MS (ESI+) M/Z 487 (M+H)+,504 (M+NH4)+.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionre-dissolved in DCM (0.80 mL)
  3. concentrationconcentrated
  4. customchromatographed (2% acetone/DCM)

Sources & evidence

ORD record
ord-323b13336334487fb4480605dfe6c95b
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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