Triethylamine → ethyl 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetate

HRID 20636

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (170 mg, 0.58 mmol, Example 7, Step 1), glycine ethyl ester•HCl (97 mg, 0.69 mmol), triethylamine (0.2 mL, 1.4 mmol), and ethanol (2 mL) was heated at 75° C. in a sealed vial for 30 h. The reaction was allowed to cool to rt, concentrated, and purified by silica gel chromatography (3:2→1:4; hexanes:ethyl acetate) to give ethyl 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetate: 1H NMR (400 MHz, DMSO-d6): δ 7.93 (t, 1H), 7.68 (d, 1H), 7.08 (d, 1H), 4.92 (s, 1H), 4.80 (m, 1H), 4.13 (q, 2H), 4.10 (d, 2H), 3.86 (s, 3H), 1.90-1.45 (m, 8H), 1.20 (t, 3H); MS (ESI): 361.9.

Workup

temperatureto cool to rt
concentrationconcentrated
custompurified by silica gel chromatography (3:2→1:4; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-9a88ae54ca854067930fc7f4ebbb20b0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745646B2

Linked notes

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