N-methyl-2-pyrrolidone → 5-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 553788Notes

Reaction equation

HRID 553788 reaction equation
CCN=C=NCCCN(C)C.[CH2:12]([N:14]1[C:18]([C:19]2[CH:20]=[C:21]([C:32](O)=[O:33])[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[CH:24]=2)=[N:17][N:16]=[N:15]1)[CH3:13].C1C=CC2N(O)N=NC=2C=1.CN1C(=O)CCC1.[CH3:52][O:53][CH2:54][CH:55]([NH2:57])[CH3:56]>C(Cl)Cl>[CH3:52][O:53][CH2:54][CH:55]([NH:57][C:32]([C:21]1[CH:22]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[CH:24]=[C:19]([C:18]2[N:14]([CH2:12][CH3:13])[N:15]=[N:16][N:17]=2)[CH:20]=1)=[O:33])[CH3:56]

Participants

7

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 123458MethoxyisopropylamineHCID 578512625-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid

Product 1

HCID 578509575-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDCI (54.0 mg, 0.282 mmol) was added in one portion to a solution of 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid (70.0 mg, 0.229 mmol), HOBt (40.0 mg, 0.296 mmol) and NMP (101.5 mg, 1.000 mmol) in CH2Cl2 (5 mL) at 0° C. After the reaction stirred at the same temperature for 1 hour, 2-methoxy-1-methyl-ethylamine (64.3 mg, 0.72 mmol) was added. The mixture was allowed to warm to room temperature and was stirred overnight. Solvent was removed under reduced pressure and the residue was purified by column chromatography to afford 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as white solid (40 mg, 46%). MS (M+H)=380.

Workup

  1. stirringwas stirred overnight
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d91f7ae0125e4b4b8bb79941ba9c6094
Source dataset
uspto-grants-2011_11
Patent number
US08048905B2

Reaction notes

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