Acetic Acid → Formate

HRID 1481259Notes

Reaction equation

HRID 1481259 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3[N:18]=[C:19]([NH:22][C:23]4[CH:24]=[N:25][N:26]([CH2:28][CH3:29])[CH:27]=4)[N:20]=[CH:21][C:16]=3[N:15]=[N:14]2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-].[C:30]([OH:33])(=[O:32])C>C1COCC1.[Zn]>[NH2:1][C:4]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]3[N:18]=[C:19]([NH:22][C:23]4[CH:24]=[N:25][N:26]([CH2:28][CH3:29])[CH:27]=4)[N:20]=[CH:21][C:16]=3[N:15]=[N:14]2)=[CH:11][CH:12]=1)([CH3:6])[CH3:5].[CH:30]([O-:33])=[O:32]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 89719369HCID 89719369, compound

Product 2

HCID 283FormateHCID 89720130HCID 89720130, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of {3-[4-(1-azido-1-methyl-ethyl)-phenyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl}-(1-ethyl-1H-pyrazol-4-yl)-amine (171 mg, 0.44 mmol) and zinc dust (117 mg, 1.79 mmol) in THF (5 ml) is added acetic acid (230 μl, 4.0 mmol) and the mixture is stirred for 16 hours at room temperature. The suspension is quenched with THF/dichloromethane/ethyl acetate. The mixture is filtered with suction and the residue is washed with methanol. The filtrate is evaporated and the residue is purified by preparative HPLC to afford {3-[4-(1-amino-1-methyl-ethyl)-phenyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl}-(1-ethyl-1H-pyrazol-4-yl)-amine (“A148”) formate salt as white powder; HPLC/MS1.32 min (A), [M+H] 364;

Workup

  1. customThe suspension is quenched with THF/dichloromethane/ethyl acetate
  2. filtrationThe mixture is filtered with suction
  3. washthe residue is washed with methanol
  4. customThe filtrate is evaporated
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-30733c8ee66545439617e8a93e3cd9eb
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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