Cyclohexylamine → HCID 11185677, compound

HRID 1294670Notes

Reaction equation

Br[C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:12]3[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]3)[CH2:8]2)=[CH:4][CH:3]=1.[CH:17]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>>[N:9]12[CH2:14][CH2:13][CH:12]([CH2:11][CH2:10]1)[CH:7]([O:6][C:5]1[CH:15]=[CH:16][C:2]([NH:23][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:3][CH:4]=1)[CH2:8]2

Participants

Reactant 2

HCID 7965Cyclohexylamine

HCID 21072608HCID 21072608, compound

Product 1

HCID 11185677HCID 11185677, compound

Procedure

The product of Example 21A (281 mg, 1.0 mmol) was treated with cyclohexylamine (Aldrich, 150 mg, 1.5 mmol) according to the procedure of Example 17A. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as oil (130 mg, yield, 43%). 1H NMR (MeOH-d4, 300 MHz) δ 1.06–1.45 (m, 6H), 1.60–1.90 (m, 5H), 1.93–2.05 (m, 3H), 2.18–2.37 (m, 2H), 3.05–3.28 (m, 5H), 4.30–4.40 (m, 1H), 6.65 (d, J=8.8 Hz, 2H), 6.74 (d, J=9.2 Hz, 2H) ppm. MS (DCl/NH3) m/z 301 (M+H)+.

Workup

customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as oil (130 mg, yield, 43%)

Sources & evidence

ORD record: ord-f723236b07934a51b84562284e831e31
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241773B2

Reaction notes

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