Triethyloxonium tetrafluoroborate → HCID 178451649, compound

HRID 712023Notes

Reaction equation

HRID 712023 reaction equation
N[C:2]([CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[NH2:27][C:28]1[C:29]([NH:37][C@H:38]2[CH2:43][CH2:42][C@H:41]([CH2:44][C:45]#[N:46])[CH2:40][CH2:39]2)=[C:30]2[S:36][CH:35]=[CH:34][C:31]2=[N:32][CH:33]=1>O1CCCC1.C(O)C.CCOC(C)=O>[C:45]([CH2:44][C@H:41]1[CH2:40][CH2:39][C@H:38]([N:37]2[C:29]3=[C:30]4[S:36][CH:35]=[CH:34][C:31]4=[N:32][CH:33]=[C:28]3[N:27]=[C:2]2[CH:4]2[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5]2)[CH2:43][CH2:42]1)#[N:46]

Participants

7

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 21307329tert-Butyl 3-carbamoylazetidine-1-carboxylateHCID 178511084HCID 178511084, compound

Product 1

HCID 178451649HCID 178451649, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 3-(aminocarbonyl)azetidine-1-carboxylate (156 mg, 0.779 mmol) and triethyloxonium tetrafluoroborate (280 mg, 1.5 mmol) in tetrahydrofuran (0.4 mL) was stirred at room temperature for 1 h and then concentrated. A mixture of {trans-4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (39 mg, 0.14 mmol) and the above made reagent in ethanol (0.70 mL) was heated at reflux for 2 h. The mixture was cooled to room temperature, diluted with EtOAc, washed with sat. NaHCO3 solution, dried over MgSO4, concentrated and purified on silica gel column (0-5% MeOH in methylene chloride) to give the desired product. LCMS calculated for C24H30N5O2S (M+H)+: m/z=452.2. Found: 452.1.

Workup

  1. concentrationconcentrated
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled to room temperature
  4. washwashed with sat. NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified on silica gel column (0-5% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-51ca3e2370e44ed7a9657857feb461c4
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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