5'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide → N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6methyl-1,1'-biphenyl-3-yl)-2-phenylpyrimidine-4-carboxamide

HRID 2114132Notes

Reaction equation

HRID 2114132 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.[C:22]1([C:28]2[N:33]=[C:32]([C:34](O)=[O:35])[CH:31]=[CH:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH:18]1([CH2:17][NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[C:5]([CH3:21])=[CH:4][CH:3]=[C:2]([NH:1][C:34]([C:32]4[CH:31]=[CH:30][N:29]=[C:28]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:33]=4)=[O:35])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamideHCID 217091412-Phenylpyrimidine-4-carboxylic acid

Product 1

HCID 69204169N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6methyl-1,1'-biphenyl-3-yl)-2-phenylpyrimidine-4-carboxamideYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (53 mg, 0.189 mmol) and 2-phenylpyrimidine-4-carboxylic acid (99.5 mg, 0.50 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 N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6methyl-1,1′-biphenyl-3-yl)-2-phenylpyrimidine-4-carboxamide (13 mg). NMR; δH CDCl3 9.98,(1H, s), 9.09,(1H, d), 8.50-8.47,(2H, m), 8.08,(1H, d), 7.86,(2H, d), 7.70,(1H, dd), 7.63,(1H, d), 7.56-7.54,(3H, m), 7.45,(2H, d), 7.33,(1H, d), 7.26,(1H, m), 3.36,(2H, m), 2.26,(3H, s), 1.09,(1H, m), 0.58,(2H, m), 0.30,(2H, m). LCMS: retention time 3.88 min, MH+463.

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-083742d3d5ec4f50942fff920d7a1ea4
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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