HCID 44578670, compound → HCID 69200756, compound

HRID 2114110Notes

Reaction equation

HRID 2114110 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][N:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[O:22])=[CH:17][CH:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:6]>N1CC=CCC1>[CH:25]1([CH2:24][NH:23][C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:11]([CH3:14])=[CH:12][CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:28]=[CH:29][N:30]=[C:2]([N:30]5[CH2:2][CH:3]=[CH:4][CH2:28][CH2:29]5)[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 1

HCID 44578670HCID 44578670, compound

Product 1

HCID 69200756HCID 69200756, compound

Reagents, catalysts & solvents 1

HCID 127501,2,3,6-TetrahydropyridineSolvent

Procedure

A solution of 2-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (50 mg, 0.12 mmol) in 1,2,3,6-tetrahydropyridine (1 ml) was heated at 120° C. for 18 h in a sealed tube. The reaction was concentrated under vacuum, the residue chromatographed on an SPE (C18) eluting with a water/acetonitrile gradient, to give after evaporation of the solvents under vacuum N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(1,2,3,6-tetrahydropyrid-1-yl)isonicotinamide. NMR; δH [2H6]—DMSO 10.31,(1H, s), 8.62,(1H, t), 8.25,(1H, d), 7.93,(2H, d), 7.72,(1H, dd), 7.65,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 7.18,(1H, s), 7.04,(1H, d), 5.90,(1H, m), 5.83,(1H, m), 3.99,(2H, m), 3.75,(2H, t), 3.16,(2H, t), 2.21,(5H, m), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.44 min, MH+467.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue chromatographed on an SPE (C18)
  3. washeluting with a water/acetonitrile gradient
  4. customto give
  5. customafter evaporation of the solvents under vacuum N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(1,2,3,6-tetrahydropyrid-1-yl)isonicotinamide

Sources & evidence

ORD record
ord-a6153015832148f1b771f9c0ae630e84
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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