Dimethylamine → HCID 59496615, compound

HRID 449500Notes

Reaction equation

HRID 449500 reaction equation
F[P-](F)(F)(F)(F)F.[CH3:8][N+:9](C)=[C:10](N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:34]([O:38][C:39]([NH:41][CH:42]([CH2:46][C:47]1[CH:48]=[N:49][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([F:59])[C:54]=2[F:60])=[CH:51][CH:52]=1)[C:43](O)=[O:44])=[O:40])([CH3:37])([CH3:36])[CH3:35].CNC.O1CCCC1>CN(C)C=O>[F:60][C:54]1[C:55]([F:59])=[CH:56][CH:57]=[CH:58][C:53]=1[C:50]1[N:49]=[CH:48][C:47]([CH2:46][CH:42]([NH:41][C:39](=[O:40])[O:38][C:34]([CH3:36])([CH3:37])[CH3:35])[C:43]([N:9]([CH3:10])[CH3:8])=[O:44])=[CH:52][CH:51]=1

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59496708HCID 59496708, compound

Product 1

HCID 59496615HCID 59496615, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (92 uL, 0.53 mmol) were added to a solution of 2-[(tert-butoxycarbonyl)amino]-3-[6-(2,3-difluorophenyl)pyridin-3-yl]propanoic acid (100 mg, 0.3 mmol) in N,N-dimethylformamide (5 mL). The reaction was stirred at r.t. for 10 min, and 2 M of dimethylamine in tetrahydrofuran (0.26 mL, 0.53 mmol) was added and stirred for 1 h. The reaction mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give crude tert-butyl 3-(6-(2,3-difluorophenyl)pyridin-3-yl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (0.06 g, 60%) as an oil. Analytical LCMS (M+H)+: m/z=406.0.

Workup

  1. stirringstirred for 1 h
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf0f7c2dd9aa44c59e574922b27d362e
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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