Hydroxylamine → HCID 58378242, compound

HRID 383453Notes

Reaction equation

HRID 383453 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:9]3[C:14]([C:15]=2[C:16]#[N:17])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[NH2:25][OH:26].[OH-].[Na+]>CS(C)=O.[Cl-].[Na+].O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)[C:9]3[C:14]([C:15]=2/[C:16](=[N:25]/[OH:26])/[NH2:17])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 787Hydroxylamine2×HCID 14798Sodium HydroxideHCID 44464311HCID 44464311, compound

Product 1

HCID 58378242HCID 58378242, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

The compound 2-(5-chlorothiophen-2-yl)-1-(4-hydroxyphenyl)-1H-indole-3-carbonitrile (Example 86) was dissolved in DMSO (0.25 mL) and hydroxylamine (0.25 mL, 100 eq) was added from a 2M stock solution of hydroxylamine*hydrochloride neutralized with sodium hydroxide (pH=7.01 as measured with pH-meter). The mixture was stirred at 60° C. for 18 hours. The cooled mixture was diluted with brine and extracted with EtOAc and subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, and identified by 1H-NMR and LC/MS. Purity was determined by analytical HPLC. ES/MS m/z: 386.3 (M+H), 384.2 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.89 (m, 1H), 7.21-7.13 (m, 4H), 7.04 (m, 1H), 7.00-6.97 (m, 3H) and 6.91 (d, 1H, J=4.0 Hz).

Workup

  1. extractionextracted with EtOAc
  2. customevaporated

Sources & evidence

ORD record
ord-ff146ccdebd4463b871c4eea37ac289a
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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