Sodium hydride → HCID 19077478, compound

HRID 964563Notes

Reaction equation

HRID 964563 reaction equation
[CH3:1][C:2]1[C:3]([C:19]([OH:21])=O)=[N:4][C:5]2[C:6]=1[C:7]([CH3:18])=[C:8]1[C:16]([CH:17]=2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[N:9]1.[C:22]([C:29]1[NH:30][CH:31]=[CH:32]N=1)([C:24]1NC=CN=1)=O.[N-:34]1C=C[N:36]=[CH:35]1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:3]([C:19]2[O:21][N:36]=[C:35]([C:24]3[CH:22]=[CH:29][N:30]=[CH:31][CH:32]=3)[N:34]=2)=[N:4][C:5]2[C:6]=1[C:7]([CH3:18])=[C:8]1[C:16]([CH:17]=2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[N:9]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3386966ImidazolateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 19367633HCID 19367633, compound

Product 1

HCID 19077478HCID 19077478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dimethylpyrrolo[3,2-b]carbazole-2-carboxylic acid (0.556 g, 2 mmol), (prepared as described in WO93/01512) and carbonyl diimidazole (0.37 g, 2.2 mmol) were dissolved in freshly distilled tetrahydrofuran (10 ml) in an oven-dried flask under a nitrogen atmosphere. The resulting orange solution was stirred at room temperature for 2 hours, by which time it was an orange suspension, and complete conversion of the acid to the imidazolide intermediate was verified by TLC. Meanwhile, in a second oven-dried flask, 4-pyridylamidoxime (0.557 g, 4.1 mmol) was dissolved in THF (20 ml). To this was added crushed 3 Å sieves (0.66 g) and the mixture was stirred at room temp for 1 hour. Sodium hydride (60% dispersion in mineral oil, 0.161 g, 4 mmol) was added and the mixture stirred for a further 1 hour. The contents of the two flasks were combined and stirred at room temp for 18 hours, by which time TLC showed complete consumption of the imidazolide intermediate. The yellow precipitate which had formed was filtered off and taken up into hot DMSO. This was filtered and water was added. On cooling, yellow crystals of the title compound formed, were filtered off and dried (vacuum oven/85° C.) (0.265 g, 35%) m.p. >300° C. (decomp.) (Found: C, 71.37; H, 4.49; N, 17.94. C23H17N5O.0.4H2O requires: C, 71.45; H, 4.64; N, 18.11%); δH [2H6 ]-DMSO 11.85 (1H, s, 1-NH), 10.70 (1H, s, 5-NH), 8.17 and 8.05 (4H, AB quart, J 5.5, pyridine), 8.13 (1H, d, J 7.5, 9-H), 7.95 (1H, s, 10-H), 7.48-7.32 (2H, m, 6-H, 7-H), 7.10 (1H, ddd, J 7.5, 5.5, 2, 8-H), 3.08 and 2.95 (2×3H, 2×s, 3-CH3 and 4-CH3); m/z (%) 379 (5, M+), 259 (42), 224 (61), 193 (100); νmax (KBr disc)/cm-1 3439, 3244, 1610, 1500, 1414, 1371, 1311, 1242.

Workup

  1. additionTo this was added
  2. customcrushed 3 Å
  3. stirringthe mixture was stirred at room temp for 1 hour
  4. stirringthe mixture stirred for a further 1 hour
  5. stirringstirred at room temp for 18 hours, by which time TLC
  6. customconsumption of the imidazolide intermediate
  7. customThe yellow precipitate which had formed
  8. filtrationwas filtered off
  9. filtrationThis was filtered
  10. additionwater was added
  11. temperatureOn cooling

Sources & evidence

ORD record
ord-bf8e5a5d86854ac3b834a56217a4563c
Source dataset
uspto-grants-1998_06
Patent number
US05770598

Reaction notes

Loading…