Dimethylamine, hydrochloride → HCID 123212539, compound

HRID 510971Notes

Reaction equation

HRID 510971 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[C:12]([O:28][CH3:29])=[C:13]([C:19]2[N:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[CH:21][CH:20]=2)[C:14]([CH3:18])=[C:15]([Cl:17])[CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:31][N:32](C(C)C)[CH:33](C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.Cl.CNC>CCOC(C)=O.CN(C=O)C>[Cl:17][C:15]1[C:14]([CH3:18])=[C:13]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([C:25]([N:32]([CH3:33])[CH3:31])=[O:26])[N:24]=2)[C:12]([O:28][CH3:29])=[C:11]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH3:10])[CH:16]=1

Participants

7

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 86666882HCID 86666882, compound

Product 1

HCID 123212539HCID 123212539, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 6-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)pyridine-2-carboxylic acid (0.07 g, 0.2 mmol) was combined with DMF (3.0 mL) and DIPEA (0.14 mL, 0.83 mmol) at room temperature and the N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.13 g, 0.33 mmol) was added. The reaction stirred for 10 min and dimethylamine hydrochloride (0.041 g, 0.50 mmol) was added. The reaction was stirred at room temperature for 3 h and was complete by LC/MS. The reaction mixture was diluted with EtOAc and washed with water, saturated ammonium chloride, brine, dried over magnesium sulfate and concentrated to give the desired product as an oil (0.06 g, 83%). LCMS calculated for C23H31ClN3O4 (M+H)+: m/z=448.2. found: 448.1.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 h
  2. washwashed with water, saturated ammonium chloride, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-df30629b4a4440b7aea63240bfd39b90
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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