Hydrochloric Acid → HCID 11709451, compound

HRID 1787581Notes

Reaction equation

HRID 1787581 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][CH:22]=[CH:23][C:16]=23)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[H-].[K+].I[CH3:27].Cl>CN(C)C=O.C(OCC)C.CCCCCC>[CH3:27][N:21]1[C:17]2=[N:18][CH:19]=[CH:20][C:15]([C:8]3[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:11][N:10]4[CH2:12][CH2:13][CH2:14][C:9]=34)=[C:16]2[CH:23]=[CH:22]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 82127Potassium hydrideHCID 11616417HCID 11616417, compound

Product 1

HCID 11709451HCID 11709451, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Dissolve 4-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (Example 1; 0.150 g, 0.50 mmol) in N,N-dimethylformamide (10 ml). Add n-hexane (2 mL) and cool to 0° C. Add potassium hydride (35% suspension in mineral oil, 0.12 g, 1.0 mmol) and stir under nitrogen at 0° C. for 5 min. Add iodomethane (0.18 g, 1.3 mmol) and stir at 0° C. for 15 min. Dilute the reaction mixture by adding 1.0M aqueous hydrochloric acid (10 mL) and with excess diethyl ether. Extract the mixture with 0.2M aqueous hydrochloric acid. Combine the acidic aqueous extracts, add 5M aqueous sodium hydroxide until basic, and extract with dichloromethane. Concentrate the organic extracts under reduced pressure and purify via chromatography (silica gel, 95% ethyl acetate/5% methanol containing 0.1M ammonia) to obtain 0.125 g (79%) of the title compound as a cream colored solid. TOF MS (ES) exact mass calculated for C19H18N5 (p+H): m/z=316.1562, Found: 316.1536.

Workup

  1. additionDilute the reaction mixture
  2. extractionExtract the mixture with 0.2M aqueous hydrochloric acid
  3. additionadd 5M aqueous sodium hydroxide until basic, and
  4. extractionextract with dichloromethane
  5. concentrationConcentrate the organic extracts under reduced pressure
  6. custompurify via chromatography (silica gel, 95% ethyl acetate/5% methanol containing 0.1M ammonia)

Sources & evidence

ORD record
ord-c24db5fb71c547d8affbbcb03f234aa4
Source dataset
uspto-grants-2009_03
Patent number
US07511056B2

Reaction notes

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