Hydroxyamine hydrochloride → HCID 11774426, compound

HRID 2223051Notes

Reaction equation

HRID 2223051 reaction equation
[CH2:1]([NH:8][C:9](=[O:37])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C@H:18]([NH:20][CH2:21][C@@H:22]([C:24]2[CH:25]=[N:26][C:27]([N:30]3C(C)=CC=C3C)=[CH:28][CH:29]=2)[OH:23])[CH3:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO>C(O)C>[NH3:8].[NH2:30][C:27]1[N:26]=[CH:25][C:24]([C@@H:22]([OH:23])[CH2:21][NH:20][C@H:18]([CH3:19])[CH2:17][C:13]2[CH:12]=[C:11]([CH2:10][C:9]([NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:37])[CH:16]=[CH:15][CH:14]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 11598476HCID 11598476, compound

Product 2

HCID 222AmmoniaHCID 11774426HCID 11774426, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-Benzyl-2-[3-((2R)-2-{(2R)-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-3-yl]-2-hydroxy-ethylamino}-propyl)-phenyl]-acetamide (preparation 1, 148 mg, 0.30 mmol) in ethanol (5 ml) was treated with hydroxylamine hydrochloride (103 mg, 1.48 mmol) and the resulting mixture heated to 85C. for 48 hours. The reaction was cooled to room temperature and passed through a Strong Cation Exchange column eluting with methanol followed by 2N ammonia in methanol to elute the product. Further purification by flash column chromatography eluting with dichloromethane:methanol: 880 ammonia (97:3:0.5 changing to 90:10:1 by volume) gave the title compound as a pale yellow solid (36 mg).

Workup

  1. washeluting with methanol
  2. washto elute the product
  3. customFurther purification by flash column chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-20866aa912a743508c44145e669ce85b
Source dataset
uspto-grants-2008_05
Patent number
US07375100B2

Reaction notes

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