Diisopropylethylamine → HCID 178446215, compound

HRID 2262692Notes

Reaction equation

HRID 2262692 reaction equation
[Cl:1][C:2]1[C:3]([CH:17]=O)=[C:4]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:9]([OH:16])=[N:8][C:5]2=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl.[NH2:29][OH:30]>C(Cl)Cl>[Cl:1][C:2]1[C:3](/[CH:17]=[N:29]/[OH:30])=[C:4]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:9]([OH:16])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 178446217HCID 178446217, compound

Product 1

HCID 178446215HCID 178446215, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

6-Chloro-2-hydroxy-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridine-7-carbaldehyde (20 mg) was dissolved in 3 mL of CH2Cl2. DIEA (130 uL, 10 eq.) and hydroxylamine hydrochloride (51.5 mg, 10 eq.) were added, and the resulting solution was stirred at 60° C. for 2 h. The solvent was evaporated, and the crude was purified by reversed phase HPLC using an acetonitrile/water gradient to give 15 mg of the desired product in 71.4% yield. m/z=283.20 [M+H]+

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-c6852ab05279479aa49112f48da7cb32
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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