Ammonia → HCID 90415177, compound

HRID 578844Notes

Reaction equation

HRID 578844 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 LC/MS 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-f956d52027ed4db38f5a551f554d8d11
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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