Diisopropylethylamine → HCID 58449363, compound

HRID 2278749Notes

Reaction equation

HRID 2278749 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:10]=1)[C:5]([OH:7])=O.[CH3:18][C:19]1[N:24]=[CH:23][C:22]([C@H:25]([NH2:27])[CH3:26])=[CH:21][N:20]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:10]=1)[C:5]([NH:27][C@@H:25]([C:22]1[CH:21]=[N:20][C:19]([CH3:18])=[N:24][CH:23]=1)[CH3:26])=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 58449374HCID 58449374, compound

Product 1

HCID 58449363HCID 58449363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with 3-bromo-5-(5-methylpyridin-2-yl)benzoic acid (250 mg, 0.86 mmol), (R)-1-(2-methylpyrimidin-5-yl)ethanamine (141 mg, 1.03 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (651 mg, 1.71 mmol), N,N-diisopropylethylamine (0.60 mL, 3.42 mmol), and N,N-dimethylformamide (6 mL). The reaction mixture was stirred at room temperature overnight, and then washed with brine and extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure to afford a light brown oil.

Workup

  1. washwashed with brine
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customto afford a light brown oil

Sources & evidence

ORD record
ord-19822be2c03d44afabf5189aa1842c44
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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