Ammonia → HCID 90415177, compound

HRID 2271486Notes

Reaction equation

HRID 2271486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][N:17]3[CH:21]=[N:20][C:19]([C:22]([O:24]C)=O)=[N:18]3)[CH:11]=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[NH3:26]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][N:17]3[CH:21]=[N:20][C:19]([C:22]([NH2:26])=[O:24])=[N:18]3)[CH:11]=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 86297745HCID 86297745, compound

Product 1

HCID 90415177HCID 90415177, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of methyl 1-((5-(3-chlorophenyl)-6-methoxypyridin-3-yl)methyl)-1H-1,2,4-triazole-3-carboxylate (Example 141, 103 mg, 0.28 mmol) in methanol (2 mL) was added ammonia in methanol (2 mL of 7N solution, 14 mmol). The mixture was heated using microwave irradiation at 130° C. for 20 min. The LCMS showed incomplete conversion. To the reaction mixture was added more ammonia in methanol (2 mL, 14 mmol) and irradiated in a microwave at 120° C. for an additional 20 min. The solvent was removed under reduced pressure. Purification (FCC, SiO2, 0-5% MeOH/DCM) afforded the title compound (77 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ 8.74 (s, 1H), 8.25 (d, J=2.3 Hz, 1H), 7.85 (d, J=2.3 Hz, 1H), 7.78-7.70 (m, 1H), 7.62-7.40 (m, 5H), 5.45 (s, 2H), 3.87 (s, 3H). [M+H]=354.18.

Workup

  1. temperatureThe mixture was heated
  2. custommicrowave irradiation at 130° C. for 20 min
  3. customirradiated in a microwave at 120° C. for an additional 20 min
  4. customThe solvent was removed under reduced pressure
  5. customPurification (FCC, SiO2, 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-ea03706828ff4e33b0ce9a8155a9beb2
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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