Thiophenol → HCID 136983947, compound

HRID 1507483Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:20][C@H:21]2[C@@H:25]3[O:26][C:27]([CH3:30])([CH3:29])[O:28][C@@H:24]3[C@@H:23]([CH2:31][OH:32])[CH2:22]2)=[N:12][C:13]([S:18][CH3:19])=[N:14][C:15]=1[O:16]C.C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>CN1C(=O)CCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([S:18][CH3:19])=[N:12][C:11]=1[NH:20][C@H:21]1[C@H:25]2[C@H:24]([O:28][C:27]([CH3:30])([CH3:29])[O:26]2)[C@@H:23]([CH2:31][OH:32])[CH2:22]1

Participants

Conditions

Temperature: 190 °C

Procedure

Compound 7 (800 mg, 1.686 mmol) and potassium carbonate (46.6 mg, 0.337 mmol) were suspended in NMP (843 μl) and thiophenol (208 μl, 2.023 mmol) was added. The reaction was sealed and heated to 190° C. for 20 min to consume all SM. The reaction was diluted with EtOAc, washed with water, brine, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with CH2C2/MeOH to give the title compound as a white solid. 1H NMR (CD3OD) δ 7.80-7.77 (m, 2H), 7.35-7.31 (m, 1H), 7.23-7.19 (m, 1H), 4.61-4.56 (m, 2H), 4.43-4.04 (m, 1H), 3.76-3.74 (m, 2H), 2.54 (s, 3H), 2.57-2.46 (m, 1H), 2.35-2.31 (m, 1H), 1.82-1.77 (m, 1H), 1.44 (s, 3H), 1.27 (s, 3H); LCMS 2.29 min, 461 (M+H)

Workup

customThe reaction was sealed
customto consume all SM
additionThe reaction was diluted with EtOAc
washwashed with water, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel
washeluting with CH2C2/MeOH

Sources & evidence

ORD record: ord-a60a36db481b4899bd4bd004e2bfef69
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221809B2

Reaction notes

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