4-Methylpiperidine → HCID 58032534, compound

HRID 405028Notes

Reaction equation

HRID 405028 reaction equation
C([O:5][C:6](=[O:46])[CH:7]([NH:30][C:31]([C:33]1[CH:34]=[C:35]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[CH:36]=[CH:37][CH:38]=1)=[O:32])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([C:20]([N:22]3[CH2:27][CH2:26][CH:25]([CH3:28])[CH2:24][CH2:23]3)=[O:21])[O:17][N:16]=2)=[C:11]([F:29])[CH:10]=1)(C)(C)C.COC(C1ON=C(C2C=CC(CC(C(OC(C)(C)C)=O)NC(C3C=C(C4C=CC(C)=CC=4)C=CC=3)=O)=CC=2F)N=1)=O.CC1CCNCC1>CO>[F:29][C:11]1[CH:10]=[C:9]([CH2:8][CH:7]([NH:30][C:31]([C:33]2[CH:34]=[C:35]([C:39]3[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=3)[CH:36]=[CH:37][CH:38]=2)=[O:32])[C:6]([OH:46])=[O:5])[CH:14]=[CH:13][C:12]=1[C:15]1[N:19]=[C:18]([C:20]([N:22]2[CH2:23][CH2:24][CH:25]([CH3:28])[CH2:26][CH2:27]2)=[O:21])[O:17][N:16]=1

Participants

5

Reactant 3

HCID 693814-MethylpiperidineHCID 66630755HCID 66630755, compoundHCID 66631055HCID 66631055, compound

Product 1

HCID 58032534HCID 58032534, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

3-{3-Fluoro-4-[5-(4-methyl-piperidine-1-carbonyl)-[1,2,4]oxadiazol-3-yl]-phenyl}-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-propionic acid tert-butyl ester. A mixture of 3-(4-{2-tert-butoxycarbonyl-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-ethyl}-2-fluoro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid methyl ester (50 mg) and 4-methyl-piperidine (13.5 mg) in MeOH (3 mL) was heated at 55° C. for 25 min in a microwave reactor. TLC showed the reaction was completed. The mixture was concentrated, 10 mL of 1N aq. HCl solution and 20 mL of ethyl acetate were added. The layers were separated and the aqueous portion was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (2×30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (40 mg, 71.4% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. addition10 mL of 1N aq. HCl solution and 20 mL of ethyl acetate were added
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with ethyl acetate (2×10 mL)
  5. washThe combined organic layers were washed with brine (2×30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-717fcc39c1b84e02a34d6153fd6cdf6a
Source dataset
uspto-grants-2014_06
Patent number
US08748412B2

Reaction notes

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