Cyclohexylamine → HCID 18446572, compound

HRID 1868331Notes

Reaction equation

Cl[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:21]#[N:22])=[CH:4][N:3]=1.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:23]1([NH:29][C:2]2[C:7]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:13][CH:12]=4)[S:10][C:6]=3[C:5]([C:21]#[N:22])=[CH:4][N:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-chloro-7-cyano-2-(4′-t-butylphenyl)-thieno[3,2-c]pyridine (0.05 g, 0.153 mmol) in DMF was added cyclohexylamine (0.017 g, 0.168 mmol) and potassium carbonate (0.023 g, 0.168 mmol). The resulting mixture was stirred under nitrogen at 80° C. for 2 h. After this time the mixture was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL), and the organic layer washed with water and brine, then dried over magnesium sulphate and concentrated under reduced pressure. Purification by silica gel chromatography (eluent 20% ethyl acetate in hexane) afforded 0.042 g of 102. 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.63 (d, 2H), 7.50 (d, 2H), 7.38 (s, 1H), 5.14 (bs, 1H), 4.20 (bs, 1H), 2.18 (m, 2H), 1.80 (m, 4H), 1.6-1.12 (m, 13H).

Workup

customAfter this time the mixture was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL)
washthe organic layer washed with water and brine
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
customPurification by silica gel chromatography (eluent 20% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-bc022de74c424f57998adcaf49bb0208
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635695B2

Reaction notes

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