Diisopropylethylamine → HCID 67324905, compound

HRID 2199310Notes

Reaction equation

HRID 2199310 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]2[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=2[CH3:26])[C:20]([OH:22])=O)=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CN>CN(C=O)C>[CH3:26][C:25]1[CH:24]=[CH:23][C:19]([C:20](=[O:22])[NH:28][CH3:27])=[CH:18][C:17]=1[NH:16][CH2:15][C:12]1[N:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67325696HCID 67325696, compound

Product 1

HCID 67324905HCID 67324905, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-((5-(tert-butoxycarbonylamino)pyrazin-2-yl)methylamino)-4-methylbenzoic acid (30 mg, 0.08 mmol) in DMF (1 mL) were added HATU (95 mg, 0.25 mmol), DIEA (74 L, 0.42 mmol) and methylamine hydrochloride (9 mg, 0.13 mmol). The reaction mixture was stirred for overnight at room temperature after which, it was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product (29 mg, 93% yield) was used without further purification. MS m/z: 372 [M+1].

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4, celite
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50c44a3623cf42eaae8a9fadf4064ef3
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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