Methanol → HCID 67342673, compound

HRID 451568Notes

Reaction equation

HRID 451568 reaction equation
[NH2:1][C:2]1[N:19]=[C:5]2[C:6]([CH:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[OH:11])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:20][C:21]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)[S:23][N:22]=1.[B][B][B][B][B][B][B][B][B][B].[CH3:43]O>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([O:11][CH3:43])[C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:1][CH:29]4[CH2:30][CH2:31][N:26]([C:24]5[S:23][N:22]=[C:21]([CH3:20])[N:25]=5)[CH2:27][CH2:28]4)[N:19]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 592585101-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-oneHCID 67343283HCID 67343283, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 67342673HCID 67342673, compoundYield 4%

Procedure

Prepared in analogy to example 219f), starting from (2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)(4-fluorophenyl)methanol and 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one. As a reducing agent 1 eq decaborane in methanol was used at 50° C. over night. The crude product was purified by column chromatography on silica gel using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent to yield eluting first {8-[(4-fluoro-phenyl)-methoxy-methyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine (yield: 4%) as a colorless oil.

Workup

  1. customPrepared in analogy to example 219f),
  2. customThe crude product was purified by column chromatography on silica gel using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent
  3. customto yield

Sources & evidence

ORD record
ord-490a78b8c454487db0e346110951f2b1
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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