Aniline → HCID 11150534, compound

HRID 1294691Notes

Reaction equation

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

Participants

Reactant 2

HCID 6115Aniline

HCID 21072621HCID 21072621, compound

Product 1

HCID 11150534HCID 11150534, compound

Procedure

The product of Example 35A (200 mg, 0.61 mmol) was treated with aniline (Aldrich, 93 mg, 1 mmol) according to the procedure of Example 17A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.20) as an oil (120 mg, yield, 68%). 1H NMR (MeOH-d4, 300 MHz) δ 1.45–1.57 (m, 1H), 1.72–1.84 (m, 2H), 1.93–2.06 (m, 2H), 2.63 (ddd, J=12.9, 5.1, 2.7 Hz, 1H), 2.82–2.99 (m, 4H), 3.30–3.40 (m, 1H), 3.56–3.64 (m, 1H), 6.56–7.13 (m, 9H) ppm. MS (DCl/NH3) m/z 294 (M+H)+.

Workup

customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.20) as an oil (120 mg, yield, 68%)

Sources & evidence

ORD record: ord-e178043f431046dbb9574d938e257102
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241773B2

Reaction notes

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