Sodium hydride → HCID 10246290, compound

HRID 457568Notes

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

Participants

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

temperatureThe reaction was cooled to RT
customquenched with methanol (10 drops)
additionSilica gel was added
customthe solvent was evaporated under reduced pressure to dryness
custompurified by silica gel chromatography
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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