Ethanol → HCID 178433368, compound

HRID 472248Notes

Reaction equation

HRID 472248 reaction equation
[Br:1][C:2]1[C:3]([NH:16][C@@H:17]2[CH2:22][CH2:21][C@H:20]([O:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]2)=[N:4][C:5]([N:9]2C(C)=CC=C2C)=[N:6][C:7]=1[CH3:8].Cl.NO.C(O)C>O>[NH2:9][C:5]1[N:4]=[C:3]([NH:16][C@@H:17]2[CH2:18][CH2:19][C@H:20]([O:23][CH2:24][CH2:25][OH:26])[CH2:21][CH2:22]2)[C:2]([Br:1])=[C:7]([CH3:8])[N:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 178433072HCID 178433072, compound

Product 1

HCID 178433368HCID 178433368, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(cis-4-(5-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-ylamino)cyclohexyloxy)ethanol (1.23 g, 2.91 mmol) and hydroxylamine hydrochloride (1.01 g, 14.5 mmol) in 10:1 ethanol:water (22.0 mL) was heated to reflux overnight. The reaction mixture was concentrated and the residue was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-4%) to afford the title compound (697 mg, 70%).

Workup

  1. temperatureto reflux overnight
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with chloroform/7 N ammonia in methanol (0-4%)

Sources & evidence

ORD record
ord-905bdc36f76b43d8a4610f4d77e52f20
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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