2-(Methoxymethyl)pyrrolidine → HCID 69200726, compound

HRID 2114113Notes

Reaction equation

HRID 2114113 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].[CH3:31][O:32][CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][NH:35]1>CS(C)=O>[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:35]5[CH2:36][CH2:37][CH2:38][CH:34]5[CH2:33][O:32][CH3:31])[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 1439532-(Methoxymethyl)pyrrolidineHCID 44578670HCID 44578670, compound

Product 1

HCID 69200726HCID 69200726, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (50 mg, 0.12 mmol) and 2-(methoxymethyl)pyrrolidine (1 ml) in DMSO (1 ml) was heated at 140° C. for 24 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-(2-methoxymethylpyrrolidin-1-yl)isonicotinamide (16 mg). NMR; δH [2H6]—DMSO 10.29,(1H, s), 8.62,(1H, t), 8.21,(1H, d), 7.93,(2H, d), 7.70,(1H, dd), 7.65,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 7.00,(1H, d), 6.89,(1H, s), 4.23,(1H, b), 3.52-3.47,(2H, m), 3.26,(5H, m), 3.16,(2H, t), 2.20,(3H, s), 2.07-1.90,(4H, m), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 2.78 min, MH+499.

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-(2-methoxymethylpyrrolidin-1-yl)isonicotinamide (16 mg)

Sources & evidence

ORD record
ord-ac2bc7a0e1164a53bcbf1f1b8d53c560
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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