(Diethylamino)sulfur trifluoride → HCID 89717376, compound

HRID 1481257Notes

Reaction equation

HRID 1481257 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].C(N(S(F)(F)[F:34])CC)C>ClCCl>[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]([F:34])([CH3:26])[CH3:25])=[CH:20][CH:19]=4)[C:13]=3[N:14]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 71666317HCID 71666317, compound

Product 1

HCID 89717376HCID 89717376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

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 dichloromethane (3 ml) is cooled to −78° C. Diethylaminosulfurtrifluoride (201 μl, 1.52 mmol) is added. The reaction mixture is allowed to reach room temperature over 1 hour. The reaction mixture is evaporated and the residue is treated with water and saturated sodium hydrogen carbonate solution. The solids are filtered off and chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford (1-ethyl-1H-pyrazol-4-yl)-{3-[4-(1-fluoro-1-methyl-ethyl)-phenyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl}-amine (“A128”) as yellow powder; HPLC/MS1.93 min (A), [M+H] 367;

Workup

  1. customThe reaction mixture is evaporated
  2. additionthe residue is treated with water and saturated sodium hydrogen carbonate solution
  3. filtrationThe solids are filtered off
  4. customchromatographed on a silica gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-81078897f52b466dbcdc20778025c4d2
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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