Triethylamine → HCID 59751038, compound

HRID 748529Notes

Reaction equation

Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=O.[CH:15]([NH2:17])=[S:16].C(N(CC)CC)C>O1CCOCC1>[S:16]1[CH:2]=[C:3]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)[N:17]=[CH:15]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one (630 mg, 3 mmol), thioformamide (30 mL, 30 mmol; described in: J. Med. Chem. 1995, 858-868) and triethylamine (0.42 mL, 3 mmol) in dioxane was heated at 110° C. for 3 h. Additional thioformamide (10 mL, 10 mmol) was added and the reaction was stirred at 110° C. for 2 h. This batch was combined with an new batch starting from 230 mg of 5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one and the combined reaction mixtures was concentrated to approximately 10 mL and an aqueous saturated sodium hydrogencarbonate solution (50 mL) was added and the solution was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and evaporated in vacuo. The crude product was purified on a silica gel column using heptane/ethyl acetate, (1:2), as the eluent to give 400 mg (35% yield) of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ 10.47 (s, 1 H), 9.15 (s, 1 H), 7.97 (s, 1 H), 7.83 (br s, 2 H), 6.87 (d, J=8 Hz, 1 H), 3.54 (s, 2 H); MS (ES) m/z 217 (M++1).

Workup

customthe combined reaction mixtures
concentrationwas concentrated to approximately 10 mL
additionan aqueous saturated sodium hydrogencarbonate solution (50 mL) was added
extractionthe solution was extracted with ethyl acetate
dry with materialThe combined organic layers were dried (Na2SO4)
customevaporated in vacuo
customThe crude product was purified on a silica gel column

Sources & evidence

ORD record: ord-9b3bf129fcb04f82aaa3ba1e0f02bef2
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399780B2

Reaction notes

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