Diisopropylethylamine → Ethyl 4'-methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)biphenyl-3-carboxylate

HRID 1845170Notes

Reaction equation

HRID 1845170 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:19](O)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:45][C:46]1[N:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][N:47]=1.C(N(CC)C(C)C)(C)C>C([O-])(O)=O.[Na+].CCOC(C)=O.C(Cl)Cl>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:8]([C:19](=[O:20])[NH:53][CH2:52][C:49]3[CH:48]=[N:47][C:46]([CH3:45])=[N:51][CH:50]=3)[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=2)=[CH:13][CH:14]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21294601(2-Methylpyrimidin-5-yl)methanamineHCID 581879575-(Ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 44223019Ethyl 4'-methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of crude 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (450 mg, 1.6 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (610 mg, 3.2 mmol), 1-hydroxybenzotriazole hydrate (240 mg, 1.6 mmol), CH2Cl2 (5 mL) were added (2-methylpyrimidin-5-yl)methanamine (290 mg, 2.4 mmol) and N,N-diisopropylethylamine (0.41 mL, 2.4 mmol). The reaction mixture was stirred at room temperature overnight, and then diluted with aq. NaHCO3 solution and EtOAc (100 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column (0-20% MeOH/CH2Cl2) to afford the title product as a white foam.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column (0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-97d7561a4eaa4f94bb3082982c572994
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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