Triethylamine → HCID 86687152, compound

HRID 1402310Notes

Reaction equation

HRID 1402310 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH2:12]3)=[N:9][N:10]=2)[CH:7]=1.CCN(CC)CC.FC(F)(F)S(O[Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])(=O)=O>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH2:13][CH2:12]3)=[N:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86687151HCID 86687151, compound

Product 1

HCID 86687152HCID 86687152, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 94a (169 mg, 0.64 mmol) and Et3N (265 μL, 1.91 mmol) in DCM (6 mL) was added triisopropylsilyl trifluoromethanesulfonate (189 μL, 0.70 mmol). The solution was stirred for 2.5 h, then diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-5% (2M NH3 in MeOH) in DCM, to give the title compound as a pale brown gum (242 mg, 90%). LCMS (Method 3): Rt 2.93 min, m/z 422 [MH+].

Workup

  1. extractionextracted with DCM
  2. customThe combined organics were dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-e41a8b01a5304b959d4274298082abf7
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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