Diisoamylamine → 2-(p-Bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylic diisopentylamide

HRID 1475936Notes

Reaction equation

HRID 1475936 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:19]=[C:11]3[CH:12]=[C:13]([C:16]([OH:18])=O)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH2:20]([NH:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:21][CH:22]([CH3:24])[CH3:23].O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+]>CN(C=O)C.ClCCl>[CH2:26]([N:25]([CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:16]([C:13]1[CH:14]=[CH:15][N:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[CH:19]=[C:11]2[CH:12]=1)=[O:18])[CH2:27][CH:28]([CH3:29])[CH3:30]

Participants

8

Reactant 5

HCID 10988DiisoamylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68276030HCID 68276030, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 683531522-(p-Bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylic diisopentylamideYield 90.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(4-bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylic acid (2.20 g, 7.0 mmol), diisopentylamine (2.13 mL, 1.64 g, 10.4 mmol) and hydroxybenzotriazole hydrate (1.59 g, 10.4 mmol) were dissolved in DMF (50 mL) and CH2Cl2 (25 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.0 g, 10.4 mmol) was added and the mixture was stirred at room temperature overnight. A saturated solution of ammonium chloride (20 mL) was added and the mixture was diluted with dichloromethane (20 mL). The separated aqueous layer was then extracted with dichloromethane (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford a residue which was purified by column chromatography using 20% to 30% EtOAc in hexanes as eluant to provide 2.89 g of the title compound. LCMS m/z 456.2, 4582 (M+H)+, ret. time=3.33 min.

Workup

  1. extractionThe separated aqueous layer was then extracted with dichloromethane (3×25 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d3b8fedf3bee4d9aa1621bade232190a
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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