Diisopropylethylamine → HCID 86677455, compound

HRID 570334Notes

Reaction equation

HRID 570334 reaction equation
[C:1]([N:3]1[CH2:6][CH:5]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:30])=[C:16]([NH:18][C:19]([C:21]4[N:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]5=[N:23][CH:22]=4)=[O:20])[CH:17]=3)[N:8]=2)[CH2:4]1)#[N:2].Cl.[NH2:32][OH:33].CCN(C(C)C)C(C)C>C(O)C>[OH:33][N:32]=[C:1]([N:3]1[CH2:4][CH:5]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:30])=[C:16]([NH:18][C:19]([C:21]4[N:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]5=[N:23][CH:22]=4)=[O:20])[CH:17]=3)[N:8]=2)[CH2:6]1)[NH2:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86677454HCID 86677454, compound

Product 1

HCID 86677455HCID 86677455, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

A stirring mixture of N-(5-(5-(1-cyanoazetidin-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (82) (50 mg, 0.125 mmol), hydroxylamine HCl (13 mg, 0.188 mmol) and DIEA (44 uL, 0.250 mmol) in ethanol was heated at 78° C. for 2 hours. The solvent was concentrated and dried under high vacuum. Crude N-(5-(5-(1-(N′-hydroxycarbamimidoyl)azetidin-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (83) was used in the next step without further purification. MS m/z 433.17 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. customdried under high vacuum
  3. customCrude N-(5-(5-(1-(N′-hydroxycarbamimidoyl)azetidin-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (83) was used in the next step without further purification

Sources & evidence

ORD record
ord-96290acb98f1447d90eb96f962fce387
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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