Triethylamine → HCID 57644083, compound

HRID 1643514Notes

Reaction equation

HRID 1643514 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([OH:16])([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])=[CH:5][N:6]=1.CCN(CC)CC.[P:24](Cl)([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:14][C:12]([F:15])([F:13])[C:7]([C:4]1[S:3][C:2]([NH:1][P:24]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25])=[N:6][CH:5]=1)([OH:16])[C:8]([F:9])([F:10])[F:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 23180662-(2-AMINO-1,3-THIAZOL-5-YL)-1,1,1,3,3,3-HEXAFLUOROPROPAN-2-OL

Product 1

HCID 57644083HCID 57644083, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-amino-1,3-thiazol-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol (133 mg 0.5 mmol) from step 1 of example 1-1-1, DMAP (61 mg, 0.5 mmol), Et3N (100 μL, 0.72 mmol) and CH2Cl2 (5 ml) was added diethyl chlorophosphate (87 μL, 06 mmol). The reaction mixture was stirred at r.t. for 96 h. Solvent was removed and EtOAc was added. The solution was washed with water. After removal of solvent, the residue was purified by a short Ion Exchange Column (Dowex-50W, ethanol) to afford the title compound as a white solid (43 mg). 1H NMR (DMSO-d6) δ 1.20 (t, 6H), 3.89 (m, 4H), 7.46 (s, 1H), 9.18 (s, 1 H); ESIMS: m/z 401 (M−H).

Workup

  1. customSolvent was removed
  2. additionEtOAc was added
  3. washThe solution was washed with water
  4. customAfter removal of solvent
  5. customthe residue was purified by a short Ion Exchange Column (Dowex-50W, ethanol)

Sources & evidence

ORD record
ord-c94b0bfcfac34b65a6463bc97c596d84
Source dataset
uspto-grants-2012_02
Patent number
US08119819B2

Reaction notes

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