Trifluoroacetic acid → HCID 89719369, compound

HRID 1481258Notes

Reaction equation

HRID 1481258 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](O)([CH3:26])[CH3:25])=[CH:20][CH:19]=4)[C:13]=3[N:14]=2)[CH:5]=[N:4]1)[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+].FC(F)(F)C(O)=O>ClCCl>[N:28]([C:24]([C:21]1[CH:22]=[CH:23][C:18]([N:15]2[C:13]3[N:14]=[C:9]([NH:8][C:6]4[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=4)[N:10]=[CH:11][C:12]=3[N:17]=[N:16]2)=[CH:19][CH:20]=1)([CH3:26])[CH3:25])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 71666317HCID 71666317, compound

Product 1

HCID 89719369HCID 89719369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 (237 mg, 0.65 mmol) and sodium azide (186 mg, 2.86 mmol) in dichloromethane (2.5 ml) is added dropwise under external cooling a solution of trifluoroacetic acid (822 μl, 10.7 mmol) in dichloromethane (2.5 ml). The reaction mixture is stirred for 18 hours at room temperature. The reaction mixture is partitioned between dichloromethane and diluted aqueous ammonia. The organic phase is dried over sodium sulfate and evaporated to afford {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 as yellow-green powder; HPLC/MS 2.01 min (A), [M+H] 390.

Workup

  1. additionis added dropwise
  2. customThe reaction mixture is partitioned between dichloromethane and diluted aqueous ammonia
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-9efbf6a40f98495cb5c40b045e67cd3a
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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