Triethylamine → HCID 87561227, compound

HRID 624167Notes

Reaction equation

HRID 624167 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:22][OH:23].C(N(CC)CC)C>C(O)C.O>[OH:23]/[N:22]=[C:1](/[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:20]2)=[O:11])=[CH:5][CH:4]=1)\[NH2:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57510058HCID 57510058, compound

Product 1

HCID 87561227HCID 87561227, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

In a 25 mL pressure tube were mixed N-(4-cyanophenyl)isoindoline-2-carboxamide (500 mg, 1.899 mmol), hydroxylamine hydrochloride (264 mg, 3.80 mmol), and triethylamine (1.323 ml, 9.50 mmol) in ethanol (6 ml)/water (0.5 ml). The reaction vessel was sealed and heated at 80° C. for four hours. The reaction mixture was diluted with water and the solid was filtered off with water washes. HPLC purification provided the title compound.

Workup

  1. customThe reaction vessel was sealed
  2. filtrationthe solid was filtered off with water washes
  3. customHPLC purification

Sources & evidence

ORD record
ord-f52c05c92b8d4e249118713704c0305f
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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