Acetic Acid → HCID 22477333, compound

HRID 1835224Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-f4735f38c0704d258e1a7fee287fb967
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770643B2

Reaction notes

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