Diisopropylethylamine → HCID 86716094, compound

HRID 627531Notes

Reaction equation

HRID 627531 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21](O)=[O:22])[CH:15]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C)C=O>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:21](=[O:22])[CH2:20][C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 736224Methyl 2-amino-5-bromobenzoateHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86716094HCID 86716094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Into a 250-mL round-bottom flask was placed a solution of methyl 2-amino-5-bromobenzoate (5 g, 21.73 mmol, 1.00 equivalent), 2-(pyridin-3-yl)acetic acid hydrochloride (4.5 g, 25.92 mmol, 1.20 equivalents), HATU (10 g, 26.30 mmol, 1.20 equivalents), and DIEA (8.5 g, 65.77 mmol, 3.00 equivalents) in N,N-dimethylformamide (100 mL). After stirring overnight at 20° C., the reaction was quenched with 100 mL of water and extracted with 3×100 mL of dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2-1:1) to give the title compound as a yellow solid.

Workup

  1. customInto a 250-mL round-bottom flask was placed
  2. customthe reaction was quenched with 100 mL of water
  3. extractionextracted with 3×100 mL of dichloromethane
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. washeluted with ethyl acetate/petroleum ether (1:2-1:1)

Sources & evidence

ORD record
ord-536c27c16e334ffd92e980ed6a6d2a70
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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