Hydrochloric Acid → HCID 136366033, compound

HRID 1821866Notes

Reaction equation

HRID 1821866 reaction equation
[C:1]1([C:7]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[N:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.[Cl:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.Cl>CN(C)C=O.C(OCC)(=O)C.C(OCC)C.O>[ClH:22].[N:25]1([CH2:24][CH2:23][O:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 136386495HCID 136386495, compound

Product 1

HCID 136366033HCID 136366033, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone oxime (Example 39) (100 mg, 0.42 mmol) and sodium hydride (17 mg of 60% in mineral oil, 0.43 mmol) in N,N-dimethyl formamide (2 mL) was stirred under a nitrogen atmosphere for 0.5 h. A mixture of N-(2-chloroethyl)morpholine hydrochloride (80 mg, 0.43 mmol) and sodium hydride (17 mg of 60% in mineral oil, 0.43 mmol) in N,N-dimethylformamide was added and the reaction mixture was stirred at room temperature for 38 h. The reaction mixture was poured into stirring cold water (25 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with water and brine, dried over sodium sulfate, and concentrated. Purification by Biotage chromatography (1 to 10% methanol in methylene chloride) produced an oil. The oil was dissolved in ethyl acetate (5 mL) and ethereal hydrogen chloride (0.45 mL of a 1 M solution in diethyl ether) was added. The reaction mixture was stirred for 1 h and the precipitate formed. The solvent was decanted and the solid was dried to give phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-[2-(4-morpholinyl)ethyl]oxime hydrochloride, a mixture of isomers, as a pale yellow solid: ESI MS m/z 351 [C20H22N4O2+H]+; HPLC (Method A) >99% (AUC), tR=13.3 and 13.7 min.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 38 h
  3. additionThe reaction mixture was poured
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by Biotage chromatography (1 to 10% methanol in methylene chloride)
  9. customproduced an oil
  10. stirringThe reaction mixture was stirred for 1 h
  11. customthe precipitate formed
  12. customThe solvent was decanted
  13. customthe solid was dried

Sources & evidence

ORD record
ord-8a8eef218d7a48b6a2bc10ca421a132c
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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