Triethylamine → HCID 11191918, compound

HRID 916711Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([C:14]([NH:17][S:18]([CH2:21][C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:19])([CH3:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)[N:5]([CH2:26][CH3:27])[N:4]=1.C([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C>CN(C)C=O.O>[CH2:26]([N:5]1[C:6]([C:8]2[CH:9]=[C:10]([C:14]([NH:17][S:18]([CH2:21][C:22]([F:23])([F:24])[F:25])(=[O:20])=[O:19])([CH3:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[CH:7][C:3]([CH2:2][N:30]2[CH2:31][CH:32]=[C:21]([C:22]([F:25])([F:24])[F:23])[CH2:34][CH2:33]2)=[N:4]1)[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

The chloride from Step 1 (45 mg, 0.106 mmol) was dissolved in dimethylformamide (3 ml) and treated with triethylamine (0.03 ml, 0.212 mmol) and the appropriate amine (20 mg, 0.108 mmol). The reaction was then heated to 80° C. for 16 hours. The reaction was then diluted with water (20 ml) and the products extracted into ethyl acetate (2×20 ml). The combined organic phase was washed with brine, dried over MgSO4 and evaporated to dryness. The product was isolated using silica gel chromatography eluting with hexane-ethyl acetate mixtures to give 0.06 g. 1H NMR (CDCl3, 360 MHz) δ 7.57-7.54 (2H, m), 7.48 (1h, t, J=7.6 Hz), 7.35 (1H, d, J=7.5 Hz), 6.26 (1H, s), 6.29 (1H, m), 5.01 (1H, brs), 4.15-4.11 (2H, q, J=7.1, 14 Hz), 3.70 (2H, s), 3.49-3.43 (2H, q, J=8.7, 17.6 Hz), 3.20 (2H, m), 2.74 (2H, t, J=5.6 Hz), 2.32 (2H, m), 1.82 (6H, s) and 1.39 (3H, t, J=7.2 Hz). MS (ES+) 539 (M+H+, 100%).

Workup

extractionthe products extracted into ethyl acetate (2×20 ml)
washThe combined organic phase was washed with brine
dry with materialdried over MgSO4
customevaporated to dryness
customThe product was isolated
washeluting with hexane-ethyl acetate mixtures
customto give 0.06 g

Sources & evidence

ORD record: ord-d2a12ed58c7b493d9614efaeb6f13fcc
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271191B2

Reaction notes

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