Dimethyl Sulfoxide → HCID 71269468, compound

HRID 1429375Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[N:14]([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)(=[O:17])=[O:16])[CH2:13][C:12]2[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=2[CH2:10][O:9][CH2:8]1)(=O)=O.CS(C)=O.C([O-])([O-])=O.[Cs+].[Cs+].[NH:42]1[CH:46]=[CH:45][CH:44]=[N:43]1>CC(=O)OCC>[N:42]1([CH2:6][C@H:7]2[N:14]([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[C:27]=3[N:26]=[CH:25][CH:24]=[CH:23]4)(=[O:16])=[O:17])[CH2:13][C:12]3[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=3[CH2:10][O:9][CH2:8]2)[CH:46]=[CH:45][CH:44]=[N:43]1

Participants

Conditions

Temperature: 110 °C

Procedure

Compound 17a (100 mg, 0.21 mmol) was added to DMSO (1 mL) and Cs2CO3 (500 mg, 1.5 mmol). 1H-Pyrazole (70 mg, 1.0 mmol) was added in the mixture and sealed in a microwave tube. The mixture was heated to 110° C. for 30 min under microwave irradiation. The reaction mixture was poured into ice/water (50 mL) and extracted with EA (3×50 mL) and washed with brine (2×50 mL) and dried over anhydrous Na2SO4. The residue was purified by CC eluting with PE:EA=3:1 to give compound 17 as white solid (30 mg, 32% yield). 1H-NMR (400 MHz, CD3OD) δ: 8.73 (d, J=1.6 Hz, 1H), 8.33 (d, J=7.2 Hz, 1H), 8.20 (d, 1H), 7.97 (d, 1H), 7.52-7.50 (m, 2H), 7.40-7.38 (m, 2H), 6.80 (d, 1H), 6.70 (t, 1H), 6.14 (s, 1H), 5.10 (m, 1H), 4.92 (d, J=14.4 Hz, 1H), 4.80 (m, 2H), 4.43 (d, J=14.4 Hz, 1H), 4.35 (q, 1H), 4.22 (q, 1H), 3.76 (d, 1H), 3.66 (d, 1H). MS (ESI+) m/z: 435.0 [M+H]+.

Workup

customsealed in a microwave tube
extractionextracted with EA (3×50 mL)
washwashed with brine (2×50 mL)
dry with materialdried over anhydrous Na2SO4
customThe residue was purified by CC
washeluting with PE

Sources & evidence

ORD record: ord-ee909b993b9649349a02cb4bb46dc130
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940722B2

Reaction notes

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