Dimethylamine → HCID 86727210, compound

HRID 2274319Notes

Reaction equation

HRID 2274319 reaction equation
[C:1]([O:4][CH:5]([C@@H:7]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:10]2[NH:11][C:12](=O)[O:13][C@H:9]2[CH2:8]1)[CH3:6])(=[O:3])[CH3:2].F[B-](F)(F)F.C[O+](C)C.[CH3:42][NH:43][CH3:44]>C(Cl)Cl>[C:1]([O:4][CH:5]([C@@H:7]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:15]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:10]2[N:11]=[C:12]([N:43]([CH3:44])[CH3:42])[O:13][C@H:9]2[CH2:8]1)[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 86727209HCID 86727209, compound

Product 1

HCID 86727210HCID 86727210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 5 (0.90 g, 2.0 mmol), trimethyloxonium tetrafluoroborate (1.5 g, 10 mmol) and 4 Å Molecular sieves (0.5 g) in DCM (5 mL) was stirred overnight at room temperature, followed by addition of dimethylamine (20 mL, 1 M in THF, 20 mmol). The reaction mixture was stirred for 12 h at room temperature, then quenched with saturated aqueous NaHCO3 (20 mL), extracted with DCM (4×50 mL). The organic layer was washed with brine (10 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give crude product 6, which was used in the next step directly. (ES, m/z): [M+H]+ 467.1.

Workup

  1. stirringThe reaction mixture was stirred for 12 h at room temperature
  2. customquenched with saturated aqueous NaHCO3 (20 mL)
  3. extractionextracted with DCM (4×50 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd68b6b22e504cf4a8f01fcae319b86f
Source dataset
uspto-grants-2015_09
Patent number
US09126957B2

Reaction notes

Loading…