Tetrahydrofuran → HCID 22253971, compound

HRID 323707Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([N:9](C(C)C)C=O)[CH2:5][CH2:4]1.[C:15]([N:23]=[C:24]=[S:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:26](N(CC)CC)C.[CH2:33]1[CH2:37][O:36]C[CH2:34]1>>[C:15]([NH:23][C:24]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:37]([CH:33]([CH3:34])[CH3:26])=[O:36])[CH2:5][CH2:4]1)=[S:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 68284Benzoyl isothiocyanate

HCID 15896073N-[4-(aminomethyl)cyclohexyl]-N-isopropylformamide

Product 1

HCID 22253971HCID 22253971, compoundYield 39%

Procedure

A mixture of N-[4-(aminomethyl)cyclohexyl]-N-isopropylformamide salt (4.55 mmol, 1 equivalent), benzoyl isothiocyanate (5.46 mmol, 1.2 equivalents) and triethylamine (5.46 mmol, 1.2 equivalents) in THF (50 ml) were stirred at room temperature overnight. The removal of solvent and chromatography afforded the desired product: 39% yield, 362 (ESMS, MH+); 1H NMR (CDCl3) δ 10.87 (broad, 1H), 9.20 (broad, 1H), 8.20 & 8.18 (two s, 1H), 7.83 (d, 2H, J=7.7 Hz), 7.60 (m, 1H), 7.49 (m, 2H), 4.26 (m, 1H), 3.76 & 3.08 (two m, 1H), 3.57 (m, 2H), 1.25 (d, 3H, J=6.8 Hz), 1.19 (d, 3H, J=6.8 Hz), 1.97-1.03(m, 9H).

Workup

customThe removal of solvent and chromatography

Sources & evidence

ORD record: ord-658d784e812944c9b4f8e3d42e19ea6c
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214853B1

Reaction notes

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