Diisopropylethylamine → HCID 86716104, compound

HRID 627542Notes

Reaction equation

HRID 627542 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]=[CH:16][C:15]=1[CH2:20][C:21](O)=[O:22].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:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 736224Methyl 2-amino-5-bromobenzoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86716104HCID 86716104, 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-2-yl)acetic acid hydrochloride (4.5 g, 25.92 mmol, 1.20 equivalent), 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 eluted with dichloromethane/methanol (1:50) to give the title compound as a red 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 dichloromethane/methanol (1:50)

Sources & evidence

ORD record
ord-3860afbd21e34a3f9bf891c554bc69a3
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

Loading…