Water → HCID 89717988, compound

HRID 1481256Notes

Reaction equation

HRID 1481256 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][C:12]3[N:17]=[N:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([OH:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=4)[C:13]=3[N:14]=2)[CH:5]=[N:4]1)[CH3:2].[OH2:28].[C:29]1([CH3:39])C=CC(S(O)(=O)=O)=CC=1.O>C(O)CO>[CH2:1]([N:3]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][C:12]3[N:17]=[N:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([CH3:26])([O:27][CH2:39][CH2:29][OH:28])[CH3:25])=[CH:20][CH:19]=4)[C:13]=3[N:14]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 71666317HCID 71666317, compound

Product 1

HCID 89717988HCID 89717988, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a suspension of 2-{4-[5-(1-ethyl-1H-pyrazol-4-ylamino)-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-phenyl}-propan-2-ol (138 mg, 0.38 mmol) in ethane-1,2-diol (1 ml) is added toluene-4-sulfonic acid monohydrate (89 mg, 0.42 mmol). The reaction mixture is stirred for 16 hours at ambient temperature. The mixture is then heated to 80° C. and the resulting clear solution is stirred at this temperature for 1 hours. The reaction mixture is cooled to room temperature and water is added. The resulting precipitate is filtered off and washed with water. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 2-(1-{4-[5-(1-ethyl-1H-pyrazol-4-ylamino)-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-phenyl}-1-methyl-ethoxy)-ethanol (“A127”) as yellow powder; HPLC/MS1.67 min (A), [M+H] 409;

Workup

  1. temperatureThe mixture is then heated to 80° C.
  2. stirringthe resulting clear solution is stirred at this temperature for 1 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with water
  6. customThe residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-820186b1cea44d4eb79c39b1490afacc
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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