tert-Butanol → HCID 57867824, compound

HRID 1686082Notes

Reaction equation

HRID 1686082 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][C:9]#[CH:10])[CH:2]=1.Cl[CH2:18][C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[N-:28]=[N+:29]=[N-:30].[Na+].C(O)(C)(C)C>O.ClCCl.[NH4+].[OH-]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][C:9]2[N:28]=[N:29][N:30]([CH2:18][C:19]3[NH:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:10]=2)[CH:2]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 33557Sodium AzideHCID 785712-ChloromethylbenzimidazoleHCID 57867840HCID 57867840, compound

Product 1

HCID 57867824HCID 57867824, compound

Reagents, catalysts & solvents 3

HCID 14923Ammonium HydroxideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

In a 0.5-2.0 mL microwave vial equipped with a spin vane were placed 3-(1-(pyridin-3-yl)but-3-ynyl)pyridine (0.030 g, 0.14 mmol), 2-chloromethylbenzimidazole (0.023 g, 0.14 mmol), NaN3 (0.0089 g, 0.14 mmol), CuSO4 pentahydrate (0.007 g, 0.03 mmol), and Cu powder (0.007 g, 0.11 mmol), tert-butanol (0.5 mL), and water (0.5 mL). The vial was sealed and warmed to 125° C. for 10 min using microwave heating. After cooling, the reaction mixture was diluted with water (1 mL), dichloromethane (2 mL) and NH4OH (two drops). The dichloromethane layer was removed and filtered, then concentrated and dried. Reverse phase chromatography yielded 0.012 g (2.3%) as a TFA salt. Analytical LCMS: single peak (214 nm), 2.209 min. HRMS m/z 382.1772 (C22H19N7+H+ requires 382.1775).

Workup

  1. customIn a 0.5-2.0 mL microwave vial equipped with a spin vane
  2. customThe vial was sealed
  3. temperatureheating
  4. temperatureAfter cooling
  5. customThe dichloromethane layer was removed
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-fa26b451db8a491fac2f7f028f98b9ed
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

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