Triethylamine → HCID 57644083, compound

HRID 2113235Notes

Reaction equation

HRID 2113235 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, 1H); 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-4fa24271fef94afb90f19be32dacf19a
Source dataset
uspto-grants-2009_04
Patent number
US07524969B2

Reaction notes

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