Potassium Hydroxide → HCID 22477527, compound

HRID 549031Notes

Reaction equation

HRID 549031 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:21][C:16]4=[N:17][CH:18]=[CH:19][N:20]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[K+].[O:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31]Cl)[CH2:26][CH2:25]1>O>[N:27]1([CH2:30][CH2:31][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[NH:21][C:16]5=[N:17][CH:18]=[CH:19][N:20]=[C:15]5[CH:14]=4)=[CH:9][CH:8]=3)[CH2:2][CH2:3]2)[CH2:28][CH2:29][O:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 767274-(2-Chloroethyl)morpholineHCID 22477181HCID 22477181, compound

Product 1

HCID 22477527HCID 22477527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6-(4-piperazin-1-ylphenyl)-5H-pyrrolo[2,3-b]pyrazine (Example 49) and water (5 mL) was treated with potassium hydroxide (71 mg) and after complete solution this mixture was then treated with morpholinoethyl chloride (59 mg) and the resulting slurry was stirred at room temperature overnight. The reaction mixture was treated with water (100 mL). and then extracted three times with ethyl acetate (100 mL). The combined extracts were washed with brine and then evaporated. The residual orange solid was treated with ethyl acetate and methanol and this solution was then acidified by addition of hydrochloric acid (2N) in methanol and then concentrated on a steam bath to give after treatment with ethyl acetate and dichloromethane the title compound (55 mg) as an orange solid. LC-MS: Method A: RT=2.09 minutes, 393 (MH+).

Workup

  1. extractionand then extracted three times with ethyl acetate (100 mL)
  2. washThe combined extracts were washed with brine
  3. customevaporated
  4. additionThe residual orange solid was treated with ethyl acetate and methanol
  5. additionthis solution was then acidified by addition of hydrochloric acid (2N) in methanol
  6. concentrationconcentrated on a steam bath

Sources & evidence

ORD record
ord-aaf08e9696b242149287eb3303dad11b
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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