Diisopropylethylamine → HCID 58447813, compound

HRID 592172Notes

Reaction equation

HRID 592172 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=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=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=3)=[CH:24][N:23]=2)=[O:11])=[CH:4][CH:3]=1

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 140715712-(6-Chloropyridin-3-yl)acetic acidHCID 200998075-(3-Fluorophenyl)pyridin-2-amine

Product 1

HCID 58447813HCID 58447813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6-chloropyridin-3-yl)acetic acid (521 mg, 3.03 mmol), 5-(3-fluorophenyl)pyridin-2-amine (570 mg, 3.03 mmol), HATU (1250 mg, 3.29 mmol) and DIEA (784 μl, 4.50 mmol) in DMF (10 ml) was stirred at room temperature overnight. DMF was mostly removed by evaporation under reduced pressure. The residue was dissolved in EtOAc (50 ml), washed with 3% Na2CO3 solution (30 ml) and water (50 mL), and dried over Na2SO4. After concentration by evaporation, the residue was subjected to silica gel column chromatography to give 2-(6-chloropyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide 140-1.

Workup

  1. customDMF was mostly removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 ml)
  3. washwashed with 3% Na2CO3 solution (30 ml) and water (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customby evaporation

Sources & evidence

ORD record
ord-3749997198ba42839a2423119b0a6602
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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