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Acetic Acid → HCID 22477333, compound

HRID 549057
Notes
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Reaction equation

HRID 549057 reaction equation
[CH3:1][NH:2][CH3:3].[C:4](O)(=O)C.C=O.[C:10]1([C:16]2[NH:24][C:19]3=[N:20][CH:21]=[CH:22][N:23]=[C:18]3[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]([CH3:4])[CH2:3][C:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][N:23]=2)[NH:24][C:16]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 3399166-Phenyl-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 22477333HCID 22477333, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dimethylamine in tetrahydrofuran (0.5 mL, 2.0M) at 0° C. was treated with glacial acetic acid (15 μl) then with formaldehyde (75 μl, 40% solution). After stirring at 0° C. for 10 minutes this mixture was treated with 6-phenyl-5H-pyrrolo[2,3-b]pyrazine [0.195 g, Example 2(c)] and then with tetrahydrofuran (3 mL) to ensure complete dissolution. The reaction mixture was allowed to warm to ambient temperature, then stirred overnight, then diluted with ethyl acetate (5 mL) and then extracted three times with hydrochloric acid (5 mL, 1N). The combined acid extracts were adjusted to pH 6-7 by addition of potassium hydroxide solution (5N). The resulting pale yellow solid was filtered, then washed with water and then dried to give the title compound (0.16 g) as a pale yellow solid, m.p. 191-192° C.

Workup

  1. dissolutiondissolution
  2. temperatureto warm to ambient temperature
  3. stirringstirred overnight
  4. extractionextracted three times with hydrochloric acid (5 mL, 1N)
  5. additionThe combined acid extracts were adjusted to pH 6-7 by addition of potassium hydroxide solution (5N)
  6. filtrationThe resulting pale yellow solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-c1ad7907793f44e4892c50b9c66dc78b
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943616B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes