Triethylamine → HCID 86700073, compound

HRID 1428119Notes

Reaction equation

HRID 1428119 reaction equation
Cl.[CH3:2][O:3][CH:4]1[CH2:7][NH:6][CH2:5]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:48][C:49]1[CH:69]=[CH:68][C:52]([CH2:53][N:54]2[CH:59]=[C:58]([C:60]([O:62][CH3:63])=[O:61])[C:57](=[O:64])[C:56]([C:65](O)=[O:66])=[CH:55]2)=[CH:51][CH:50]=1>ClCCl.CN(C=O)C.C(OCC)(=O)C.O>[F:48][C:49]1[CH:50]=[CH:51][C:52]([CH2:53][N:54]2[CH:55]=[C:56]([C:65]([N:6]3[CH2:7][CH:4]([O:3][CH3:2])[CH2:5]3)=[O:66])[C:57](=[O:64])[C:58]([C:60]([O:62][CH3:63])=[O:61])=[CH:59]2)=[CH:68][CH:69]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 222428583-Methoxyazetidine hydrochlorideHCID 86700046HCID 86700046, compound

Product 1

HCID 86700073HCID 86700073, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

3-Methoxyazetidine hydrochloride (67 mg), 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (206 mg) and triethylamine (100 μl) were added to a solution of the compound obtained in Step 2 of Example 26 (110 mg) in dichloromethane/DMF (2.0/0.5 ml) at room temperature, and the mixture was stirred for seven hours. After adding a small amount of water, the mixture was diluted with ethyl acetate, followed by drying over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->20:1 (v/v)] to give 63 mg of the title compound as an oily substance.

Workup

  1. dry with materialby drying over sodium sulfate
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->20:1 (v/v)]

Sources & evidence

ORD record
ord-dc91c4ab874b49949a99d6081ccaa11f
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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