Pyridine → HCID 85801373, compound

HRID 1829976Notes

Reaction equation

[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]1[C:13](Cl)=[O:14].Cl.[NH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23].N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:19]([CH2:20][CH2:21][CH2:22][NH:23][C:13]([C:6]1[N:5]([CH2:4][CH2:3][CH:2]([CH3:16])[CH3:1])[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=1)=[O:14])#[N:18]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of the acid chloride 45 (0.6 g, 2.45 mmol) and 3-aminopropylcyanide hydrochloride (0.31 g, 2.57 mmol) in anhydrous toluene was added 1.5 ml of anhydrous pyridine. The reaction mixture was stirred at 50° C. overnight and then evaporated to dryness. The product was purified by chromatography using toluene-ethyl acetate (2:1) to yield white crystals (0.623 g, 87%). 1H NMR (DMSO-d6) δ 8.46 (t, 1H), 8.17 (d, 1H), 7.39 (d, 1H), 4.37 (t, 2H), 3.27 (quintet, 2H), 2.53 (d, 2H), 1.77 (quintet, 2H), 1.60–1.42 (q and quintet, 3H), 0.87 (d, 6H).

Workup

customevaporated to dryness
customThe product was purified by chromatography

Sources & evidence

ORD record: ord-a8477d73543146769fb61f186a6d4d37
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064218B2

Reaction notes

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