Acetic Acid → HCID 178478068, compound

HRID 2174730Notes

Reaction equation

HRID 2174730 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:9][C:8]=2[C:18]([NH2:20])=O)=[CH:4][CH:3]=1.COC(OC)[N:26]([CH3:28])C.C(O)(=O)C.[NH2:35]N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:9][C:8]=2[C:18]2[NH:26][CH:28]=[N:35][N:20]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 56642748HCID 56642748, compound

Product 1

HCID 178478068HCID 178478068, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-(4-chlorobenzyl)-2-pyridin-4-yl-1,3-oxazole-4-carboxamide (0.130 g, 0.41 mmol) and 1,1-Dimethoxy-N,N-dimethylmethanamine (3.0 mL, 22 mmol) in Toluene (25 mL) was heated under argon at 40° C. overnight. The reaction mixture was then concentrated to an oily residue. Acetic acid (20 mL, 350 mmol) and Hydrazine (1.0 mL, 30 mmol) were added to the flask and the mixture was heated 60° C. for another 1 hour. The mixture was concentrated and the residue was purified by HPLC to afford 4-[5-(4-chlorobenzyl)-4-(4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]pyridine (7 mg, 5. 2%). LCMS (FA) ES+338.0, 339.9. 1H NMR (400 MHz, MeOD) δ ppm 8.73-8.64 (m, 2H), 8.49-8.33 (m, 1H), 8.05-7.97 (m, 1H), 7.89-7.75 (m, 2H), 7.38 (d, J=7.16 Hz, 2H), 7.30 (d, J=6.64 Hz, 2H), 4.60 (s, 2H).

Workup

  1. concentrationThe reaction mixture was then concentrated to an oily residue
  2. temperaturethe mixture was heated 60° C. for another 1 hour
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-31bca1c276fc4ddd944569faa9406025
Source dataset
uspto-grants-2015_06
Patent number
US09062038B2

Reaction notes

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