Dichloromethane → 7-[2-(3-Fluoro-pyridin-2-YL)-imidazol-1-ylmethyl]-2-isopropyl-8-propyl-[1,2,4]triazolo[1,5-C]pyrimidine

HRID 916652Notes

Reaction equation

HRID 916652 reaction equation
[C:1](OC(=O)C(C)C)(=O)[CH:2](C)[CH3:3].[F:12][C:13]1[C:14]([C:19]2[N:20]([CH2:24][C:25]3[N:30]=[CH:29][N:28]=[C:27]([NH:31][NH2:32])[C:26]=3[CH2:33][CH2:34][CH3:35])[CH:21]=[CH:22][N:23]=2)=[N:15][CH:16]=[CH:17][CH:18]=1.[CH2:36](Cl)Cl>O=P(Cl)(Cl)Cl>[F:12][C:13]1[C:14]([C:19]2[N:20]([CH2:24][C:25]3[N:30]=[CH:36][N:31]4[N:32]=[C:29]([CH:2]([CH3:3])[CH3:1])[N:28]=[C:27]4[C:26]=3[CH2:33][CH2:34][CH3:35])[CH:21]=[CH:22][N:23]=2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7346Isobutyric anhydrideHCID 57503304{6-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine

Product 1

HCID 113264467-[2-(3-Fluoro-pyridin-2-YL)-imidazol-1-ylmethyl]-2-isopropyl-8-propyl-[1,2,4]triazolo[1,5-C]pyrimidine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Isobutyric anhydride (0.5 mL) is added to a mixture of 131 (45 mg) in methylene chloride (10 mL). The mixture is stirred at room temperature for 1 hour. The solvent is removed to get residue, LC-MS (M+1) 398.17. The residue is dissolved in POCl3 (1 mL), and the mixture is heated at 85° C. for 1 hour. Excess POCl3 is removed. The residue is dissolved in methylene chloride, and washed with sat. NaHCO3, dried, and purified by TLC with 5% MeOH in methylene chloride to give the title product (156). 1H NMR δ (CDCl3) 1.02 (t, 3H, J=5.4 Hz), 1.43 (d, 6H, J=6.0 Hz), 1.71 (p, 2H, J=5.4 Hz), 2.93 (m, 2H), 3.29 (sep, 1H, J=6.0 Hz), 5.57 (s, 2H), 7.22–7.36 (m, 2H), 7.70–7.82 (m, 2H), 8.82 (d, 1H, J=3.3 Hz), 9.04 (s, 1H). LC-MS (M+1) 380.17.

Workup

  1. customThe solvent is removed
  2. customto get residue, LC-MS (M+1) 398.17
  3. temperaturethe mixture is heated at 85° C. for 1 hour
  4. customExcess POCl3 is removed
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with sat. NaHCO3
  7. customdried
  8. custompurified by TLC with 5% MeOH in methylene chloride

Sources & evidence

ORD record
ord-df15b12533124629ae2bcb4c1a277cb6
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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