HCID 2325055, compound → HCID 69201728, compound

HRID 2114133Notes

Reaction equation

HRID 2114133 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[Cl:22][C:23]1[C:24]([C:35](O)=[O:36])=[N:25][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:27][CH:28]=1>C1COCC1>[Cl:22][C:23]1[C:24]([C:35]([NH:1][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]4[CH2:20][CH2:19]4)=[O:15])=[CH:10][CH:9]=3)[C:5]([CH3:21])=[CH:4][CH:3]=2)=[O:36])=[N:25][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:27][CH:28]=1

Participants

4

Reactant 2

HCID 2325055HCID 2325055, compoundHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 69201728HCID 69201728, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (53 mg, 0.189 mmol) and 5-chloro-2-(piperidin-1-yl)pyrimidine-4-carboxylic acid (91.3 mg, 0.38 mmol) were mixed in THF (5 ml) and the mixture shaken in a varian tube for 15 min at room temperature. Carbodiimde resin (500 mg) was added and shaking continued for 48 h. The solution was filtered off and concentrated under vacuum. The residue was chromatographed on a silica gel flash column eluting with ethyl acetate/hexane (1:1) and the solvent evaporated under vacuum to give 5-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(piperidin-1-yl)pyrimidine-4- carboxamide (35 mg). NMR; δH CDCl3 9.50,(1 H, s), 8.40,(1 H, s), 7.83,(2H, d), 7.64,(1H, dd), 7.56,(1H, d), 7.41,(2H, d), 7.27,(1H, d), 6.24,(1H, t), 3.79,(4H, m), 3.35,(2H, m), 2.22,(3H, s), 1.65,(4H, m), 1.08,(1H, m), 0.82,(2H, m), 0.58,(2H, m), 0.30,(2H, m). LCMS: retention time 3.96 min, MH+504.

Workup

  1. stirringshaking
  2. waitcontinued for 48 h
  3. filtrationThe solution was filtered off
  4. concentrationconcentrated under vacuum
  5. customThe residue was chromatographed on a silica gel flash column
  6. washeluting with ethyl acetate/hexane (1:1)
  7. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-02ae794d365f49c9957cdf9468ebf058
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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