Pyridine → HCID 72703516, compound

HRID 1055026Notes

Reaction equation

HRID 1055026 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]([F:27])([F:26])[F:25])[C:5]2[N:6]([N:9]=[C:10]([CH2:12][CH2:13][C:14]3[NH:18][N:17]=[C:16]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:15]=3)[N:11]=2)[C:7]=1[CH3:8].[CH:28]1(B(O)O)[CH2:30][CH2:29]1.N1C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:24]([F:25])([F:27])[F:26])[C:5]2[N:6]([N:9]=[C:10]([CH2:12][CH2:13][C:14]3[N:15]=[C:16]([N:19]4[CH2:20][CH2:21][CH2:22][CH2:23]4)[N:17]([CH:28]4[CH2:30][CH2:29]4)[N:18]=3)[N:11]=2)[C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2760897Cyclopropylboronic acidHCID 90017353HCID 90017353, compound

Product 1

HCID 72703516HCID 72703516, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-5-methyl-2-(2-(3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (30 mg, 75.0 μmol, Eq: 1.00), cyclopropyl-boronic acid (19.3 mg, 225 μmol, Eq: 3), copper (II) acetate (27.3 mg, 150 μmol, Eq: 2), molecular sieves, pyridine (47.5 mg, 48.6 μl, 600 μmol, Eq: 8), triethylamine (38.0 mg, 52.3 μl, 375 μmol, Eq: 5) in tetrahydrofuran (4 ml) was heated under air in a sealed tube for 2 h at 100° C. The mixture was filtered and concentrated to an oil. Water was added and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and then concentrated. The mixture was separated by preparative HPLC to give the product (4.8 mg, 14.5%) as a colorless oil. MS: m/z=440.2 (M+H+)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to an oil
  3. additionWater was added
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe mixture was separated by preparative HPLC

Sources & evidence

ORD record
ord-28d6a03a426e432ab867c992244b3ba8
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…