Pyridine → HCID 86708106, compound

HRID 1497795Notes

Reaction equation

HRID 1497795 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][Cl:8])=[O:3].[NH2:9][C:10]1[N:42]=[C:13]2[C:14]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=3)=[C:15]([CH3:31])[C:16]([C:18]3[N:22]([C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)[N:21]=[CH:20][CH:19]=3)=[CH:17][N:12]2[N:11]=1.N1C=CC=CC=1>C1COCC1>[Cl:8][CH2:7][CH2:6][CH2:5][O:4][C:2](=[O:3])[NH:9][C:10]1[N:42]=[C:13]2[C:14]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=3)=[C:15]([CH3:31])[C:16]([C:18]3[N:22]([C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)[N:21]=[CH:20][CH:19]=3)=[CH:17][N:12]2[N:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 730509764-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

Product 1

HCID 86708106HCID 86708106, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloropropyl chloroformate (133 μL, 1.089 mmol) was added to a mixture of 4-{5-[2-amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 1, 100 mg, 0.218 mmol) and pyridine (107 μL, 1.308 mmol) in THF (3 mL) and the mixture was stirred rapidly for 20 mins at RT then heated at 60° C. 20 mins using microwave irradiation. The reaction mixture was concentrated in vacuo to give the title compound (125 mg of impure product contains chloroformate).

Workup

  1. temperaturethen heated at 60° C
  2. custom20 mins
  3. custommicrowave irradiation
  4. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e151e40ae7834ed6bf821620a5ad9459
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

Loading…