Triethylamine → HCID 44578670, compound

HRID 2114094Notes

Reaction equation

HRID 2114094 reaction equation
N[C:2]1[C:3]([C:15]([NH:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)=[O:16])=[CH:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[CH:7]=1.[Cl:22][C:23]1[CH:28]=[C:27]([C:29](Cl)=[O:30])[CH:26]=[CH:25][N:24]=1.C([N:34](CC)CC)C>C(Cl)Cl>[Cl:22][C:23]1[CH:28]=[C:27]([CH:26]=[CH:25][N:24]=1)[C:29]([NH:34][C:12]1[CH:13]=[C:8]([C:6]2[CH:5]=[CH:4][C:3]([C:15]([NH:17][CH2:18][CH:19]3[CH2:21][CH2:20]3)=[O:16])=[CH:2][CH:7]=2)[C:9]([CH3:14])=[CH:10][CH:11]=1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 69204142HCID 69204142, compound

Product 1

HCID 44578670HCID 44578670, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (260 mg, 0.93 mmol), 2-chloropyridine-4-carbonyl chloride (245 μl) and triethylamine (195 μl, 1.39 mmol) were stirred at room temperature in DCM (20 ml) for 72 h. The reaction was diluted with DCM (100 ml), washed with aqueous sodium hydroxide (2M, 100 ml) and dried (magnesium sulphate). The solvent was evaporated under vacuum, the residue dissolved in methanol and purified by SPE (C18, 10 g) eluting with water, water/acetonitrile (1:1) and acetonitrile. The solvent was evaporated from the product fractions under vacuum to give 2-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (130 mg, 33%). NMR; δH [2H6]—DMSO 10.57,(1H, s), 8.63-8.60,(2H, m), 7.99,(1H, s), 7.93,(2H, d), 7.86,(1H, dd),7.70,(1H, dd), 7.66,(1H, d), 7.44,(2H, d), 7.32,(1H, d), 3.16,(2H, t), 2.21,(3H, s), 1.05,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.53 min, MH+420/422.

Workup

  1. washwashed with aqueous sodium hydroxide (2M, 100 ml)
  2. dry with materialdried (magnesium sulphate)
  3. customThe solvent was evaporated under vacuum
  4. dissolutionthe residue dissolved in methanol
  5. custompurified by SPE (C18, 10 g)
  6. washeluting with water, water/acetonitrile (1:1) and acetonitrile
  7. customThe solvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record
ord-2ac35c9867054a999adfce4518ba9696
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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