Water → HCID 57652719, compound

HRID 1013271Notes

Reaction equation

HRID 1013271 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([N:18]3[CH:22]=[N:21][N:20]=[N:19]3)[CH:17]=2)[C:12]([OH:14])=O)=[N:5][CH:6]=[CH:7][CH:8]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[F:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][NH2:44])=[CH:38][CH:37]=1.O>CN1C(=O)CCC1>[F:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][NH:44][C:12](=[O:14])[C:11]2[CH:15]=[C:16]([N:18]3[CH:22]=[N:21][N:20]=[N:19]3)[CH:17]=[C:9]([C:4]3[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]=3)[CH:10]=2)=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4653p-FluorophenethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 57652718HCID 57652718, compound

Product 1

HCID 57652719HCID 57652719, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3-(3-Methoxy-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid (140 mg) and dissolved in dry NMP (15 mL), and CDI (80 mg, 0.49 mmol) was added. The reaction mixture was stirred for 40 minutes, and then 2-(4-fluorophenyl)-ethylamine (0.16 mL, 1.22 mmol) was added. The reaction mixture was stirred for 24 hours at room temperature, and then poured into 30 mL water. The resulting mixture was extracted with EtOAc, and the combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography using EtOAc/hexanes (30%-100%) to give 15 mg of N-[2-(4-fluoro-phenyl)-ethyl]-3-(3-methoxy-pyridin-2-yl)-5-tetrazol-1-yl-benzamide, MS (M+H)=419.

Workup

  1. stirringThe reaction mixture was stirred for 24 hours at room temperature
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-a15b7c0447594d6a95f6928e903a9edd
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

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