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Sodium hydride → HCID 10246290, compound

HRID 457568
Notes
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Reaction equation

HRID 457568 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.Cl[C:18]1[O:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:21][N:22]=1>C1COCC1>[CH3:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:16]=[CH:15][C:13]([NH:14][C:18]3[O:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][N:22]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 109976262-Chloro-5-phenyloxazole

Product 1

HCID 10246290HCID 10246290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60% in mineral oil, 0.51 g, 0.013 mol) was suspended in dry THF (8 mL) under an atmosphere of nitrogen. The suspension was treated with 4-(4-methylpiperazin-1-yl)-aniline (0.23 g9 1.0 mmol) and 2-chloro-5-phenyl-1,3-oxazole (0.19 g, 1.0 mmol) and heated to 60° C. and stirred for 18 h. The reaction was cooled to RT and quenched with methanol (10 drops). Silica gel was added and the solvent was evaporated under reduced pressure to dryness and purified by silica gel chromatography using 10% methanol in dichloromethane to elute the title compound (0.10 g, 31%). 1H NMR (400 MHz, d6-DMSO): δ 2.21 (s, 3H), 2.45 (m, 4H), 3.04 (m, 4H), 6.91 (d, J=8.97, 2H), 7.24 (t, J=7.32, 1H), 7.41 (m, 3H), 7.47 (d, J=8.97, 2H), 7.55 (d, J=7.51, 2H), 9.99 (s, 1H). MS (ES+, m/z)=335 (m+H)+.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customquenched with methanol (10 drops)
  3. additionSilica gel was added
  4. customthe solvent was evaporated under reduced pressure to dryness
  5. custompurified by silica gel chromatography
  6. washto elute the title compound (0.10 g, 31%)

Sources & evidence

ORD record
ord-99d794e328d4425695d59f81bc210787
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07189712B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes