Dimethylamine, hydrochloride → HCID 485755, compound

HRID 2305666Notes

Reaction equation

HRID 2305666 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=O)=[C:14]([F:21])[CH:13]=2)[CH2:7]1)(=S)[CH3:2].F[P-](F)(F)(F)(F)F.N1([O:38]C(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C[CH2:47][N:48]([CH:52](C)C)C(C)C.Cl.CNC>CN(C=O)C>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:48]([CH3:52])[CH3:47])=[O:20])=[C:14]([F:21])[CH:13]=2)[CH2:7]1)(=[O:38])[CH3:2]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59905892HCID 59905892, compound

Product 1

HCID 485755HCID 485755, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(S)-thioacetamidomethyl-3-(4′-carboxy-3′-fluorophenyl)oxazolidine-2-one (0.33 g, 1.06 mmol; prepared as described in Example 13), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (0.428 g, 1.1 mmole) and N,N′-diisopropylethylamine (0.38 ml, 2.1 mmol) in DMF (1.5 ml) was stirred at r.t. for 20 min. Dimethylamine hydrochloride (96 mg, 1.2 mmole) was added, and the mixture stirred at r.t. overnight. Solvent was removed under vacuum, and the product purified by by silica gel PTLC (eluent: 10% MeOH in ethyl acetate). White crystals (117 mg, 33%). HPLC Rt=4.2. MS (m/z): [M+H]+=340.

Workup

  1. stirringthe mixture stirred at r.t. overnight
  2. customSolvent was removed under vacuum
  3. customthe product purified by by silica gel PTLC (eluent: 10% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-9c1834d608ab43098f40614ada45466b
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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