Acetyl chloride → HCID 86711925, compound

HRID 1475232Notes

Reaction equation

HRID 1475232 reaction equation
C(Cl)(=O)C.[CH3:5][C:6]1[N:10]([CH2:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[O:15][CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[N:9]=[C:8]([C:29]2[O:33][N:32]=[C:31]([C:34]3[CH:39]=[CH:38][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=3)[N:30]=2)[N:7]=1>CO>[NH2:18][CH2:17][CH2:16][O:15][C:14]1[CH:13]=[C:12]([CH2:11][N:10]2[C:6]([CH3:5])=[N:7][C:8]([C:29]3[O:33][N:32]=[C:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][C:41]([F:42])([F:43])[F:44])=[CH:36][CH:35]=4)[N:30]=3)=[N:9]2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86711926HCID 86711926, compound

Product 1

HCID 86711925HCID 86711925, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (229 uL, 3.21 mmol) was added dropwise to MeOH (1.1 mL) at 0° C., and the resulting mixture was stirred at 0° C. for 1 hr. Tert-butyl (2-(3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenoxy)ethyl)carbamate (Example 67; 60.0 mg, 0.107 mmol) was the added in one portion, and the reaction mixture was stirred at RT for 16 h and then concentrated under reduced pressure; the residue was purified using Prep-HPLC to furnish the title compound; MS (ES+) C2iH19F3N6O3 requires: 460. found 461 [M+H]+; 1H-NMR (600 MHz, CD3OD) δ ppm 8.17 (d, J=8.6 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 7.17 (m, 1H), 6.78 (d, J=7.9 Hz, 1H), 6.73 (d, J=8.2 Hz, 1H), 6.67 (s, 1H), 5.32 (s, 2H), 4.06 (m, 2H), 3.21 (m, 2H), 2.47 (s, 3H).

Workup

  1. additionadded in one portion
  2. stirringthe reaction mixture was stirred at RT for 16 h
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified

Sources & evidence

ORD record
ord-d41d7c917f8c4008847a441726e18755
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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