Potassium Carbonate → HCID 178427315, compound

HRID 549051Notes

Reaction equation

HRID 549051 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[C:4]([C:13]2[N:21]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:3]1.Cl.[NH2:33][OH:34].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:34][NH:33][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[CH:3]=[C:4]2[C:13]1[N:21]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1)=[NH:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 22477547HCID 22477547, compound

Product 1

HCID 178427315HCID 178427315, compoundYield 123.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indole-5-carbonitrile [2.11 g, Reference Example 13(c)] in ethanol (150 mL) at ambient temperature was treated with hydroxylamine hydrochloride (1.72 g) and potassium carbonate (3.43 g). The reaction mixture was heated at reflux under nitrogen for 15 hours then filtered. The filtrate was evaporated to give the title compound (2.8 g) as a dark green solid. MS: 460 (MH+). HPLC (METHOD A): RT=6.19 minutes.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 15 hours
  3. filtrationthen filtered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-82b0e42b6cf642eda4f6951802e83187
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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