Methanol → HCID 22629674, compound

HRID 277053Notes

Reaction equation

HRID 277053 reaction equation
[BH4-].[Li+].C[Si](C)(C)Cl.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([NH:19][C:20]1[N:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=[C:24]2[CH:23]=[C:22]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[CH:21]=1)=O.CO>O1CCCC1>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][NH:19][C:20]1[N:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=[C:24]2[CH:23]=[C:22]([C:35]2[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 22629715HCID 22629715, compound

Product 1

HCID 22629674HCID 22629674, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 10 ml of a 1 molar solution of lithiumborohydride in tetrahydrofuran were added 2.17 g (0.02 mol) trimethylchlorosilane. After stirring for one hour at room temperature the suspension was added dropwise to a suspension of 0.11 g (0.25 mol) 2-(2-methoxy-phenyl)-N-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-acetamide and the mixture heated for 18 hours at 50° C. Then 5 ml methanol were slowly added, the solvents were distilled off and the residue taken up in ethylacetate. The solution was washed with aqueous sodiumhydroxide and with water, dried with sodiumsulfate and evaporated. Recrystallisation from ethanol yielded 0.10 g (94%) [2-(2-methoxy-phenyl)-ethyl]-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine as beige crystals. MS m/e(%):422 (M+H+, 100).

Workup

  1. temperaturethe mixture heated for 18 hours at 50° C
  2. distillationthe solvents were distilled off
  3. washThe solution was washed with aqueous sodiumhydroxide and with water
  4. dry with materialdried with sodiumsulfate
  5. customevaporated
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-5191959817d0463bbe4183bb7fbecd5f
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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