Methylamine → HCID 70945143, compound

HRID 518011Notes

Reaction equation

HRID 518011 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:15][N:16]1[C:24]2[CH:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33]=O)=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=3)[N:21]=[C:20]([C:39]#[N:40])[C:19]=2[N:18]=[N:17]1.[CH3:41][NH2:42]>C1COCC1.C(OCC)(=O)C>[CH3:15][N:16]1[C:24]2[CH:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][NH:42][CH3:41])=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=3)[N:21]=[C:20]([C:39]#[N:40])[C:19]=2[N:18]=[N:17]1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86673358HCID 86673358, compound

Product 1

HCID 70945143HCID 70945143, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaB(OAc)3H (640 mg) was added in portions to the solution of methyl-6-(4-(3-oxopropyl)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile, methylamine (1.5 ml, 2M in methanol) in THF (5 ml). The mixture was stirred at rt for 3 hours, then diluted with ethyl acetate (100 ml), washed with sodium carbonate (100 ml), brine (100 ml), dried over sodium sulphate, solvent removed. The crude product was used for next step without further purification (260 mg). MS m/z 375 (M+H).

Workup

  1. washwashed with sodium carbonate (100 ml), brine (100 ml)
  2. dry with materialdried over sodium sulphate, solvent
  3. customremoved
  4. customThe crude product was used for next step without further purification (260 mg)

Sources & evidence

ORD record
ord-c53f27c6fed54a86996178541f6d66de
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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