Tetrahydrofuran → HCID 22066046, compound

HRID 1828316Notes

Reaction equation

HRID 1828316 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7](/[C:10](=[N:18]/[NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])/[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O1CCCC1.[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=O)=[CH:38][CH:37]=1>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]2[N:19]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[N:18]=[C:10]([CH:7]3[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]3)[C:11]=2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 85014-Chlorobenzoyl chlorideHCID 58648728HCID 58648728, compound

Product 1

HCID 22066046HCID 22066046, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

This reaction was carried out in a 100 ml round bottom flask. N′-[(1E)-1-(1-acetylpiperidin-4-yl)-2-pyrimidin-4-ylethylidene]-4-methylbenzenesulfonohydrazide (7) (5g, 11 mmol) was charged to the reactor, followed by tetrahydrofuran (“THF”, 31 ml), which, in turn, was followed by 2.15 ml of triethylamine (“TEA”, 2.15 ml) and 4-dimethylaminopyridine (“DMAP”, 0.134 g). 4-Chlorobenzoyl chloride (8) (“4-CBC”, 2.09 ml) was then charged all at once while stirring the mixture. The reaction was brought to reflux. Liquid chromatography indicated that the reaction was complete in just over 1 hr. The solution was washed with saturated ammonium chloride (2×25 ml), and the THF was removed in vacuo to yield a yellow oil (11.18 g), which solidified upon sitting. Recrystallization from ethanol/water yielded 4.88 g of a white powder (76% yield). The product had the following characteristics: 1H NMR (CDCl3, 300 MHz) δ 9.20 (1H, s), 7.63 (2H, d, J=8.4 Hz), 7.45 (2H, d, J=8.4 Hz), 7.30 (2H, d, J=8.1 Hz), 7.29 (1H, s), 7.21 (2H, d, J=8.4 Hz), 6.64 (1H, d, J=5.1 Hz), 4.71–4.52 (1H, m), 4.01–3.82 (1H, m), 3.59–3.44 (1H, m), 3.28–3.08 (1H, m), 2.84–2.58 (1H, m), 2.46 (3H, s), 2.16 (3H, s), 2.02–1.62 (4H, m). 13C NMR (CDCl3, 75 MHz) δ 169.11, 158.91, 146.39, 136.80, 134.55, 132.01, 130.13, 129.19, 126.72, 34.91, 31.15, 22.01, 21.69.

Workup

  1. customThis reaction was carried out in a 100 ml round bottom flask
  2. temperatureto reflux
  3. customjust over 1 hr
  4. washThe solution was washed with saturated ammonium chloride (2×25 ml)
  5. customthe THF was removed in vacuo

Sources & evidence

ORD record
ord-c1bc1490af854e9195c2fa356089e051
Source dataset
uspto-grants-2006_06
Patent number
US07057049B2

Reaction notes

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