HCID 53627663, compound → HCID 53627662, compound

HRID 1876725Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C@H:11]1[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]4[S:27][CH:28]=[CH:29][N:30]=4)(=[O:24])=[O:23])=[CH:18][CH:17]=3)[C:12]1=[O:31])[CH2:6][CH2:5]2>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C@H:11]1[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]4[S:27][CH:28]=[CH:29][N:30]=4)(=[O:23])=[O:24])=[CH:18][CH:17]=3)[C:12]1=[O:31])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of (S)-4-(3-(5-chloroindolin-1-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (11 mg, 0.023 mmol) and activated MnO2 (20 mg, 0.23 mmol) in CH2Cl2 (1.0 mL) was heated to 50° C. for 20 h. After cooling to RT, the reaction mixture was filtered through a syringe filter, concentrated and dissolved in DMSO/MeOH (1:1, 0.8 mL). Purification via reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) gave (S)-4-(3-(5-chloro-1H-indol-1-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide. 1H NMR (400 MHz, MeOD-d4) δ 7.83 (d, J=3.8 Hz, 2H), 7.81 (d, J=2.5 Hz, 2H), 7.46 (d, J=2.0 Hz, 1H), 7.29-7.26 (m, 2H), 7.04-6.99 (m, 2H), 6.62 (d, J=4.7 Hz, 1H), 6.43 (d, J=3.2 Hz, 1H), 5.51 (dd, J=8.9, 11.0 Hz, 1H), 3.99 (dd, J=6.1, 9.7 Hz, 2H), 2.75-2.67 (m, 1H), 2.48-2.38 (m, 1H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=473.2; tR=3.21 min.

Workup

temperatureAfter cooling to RT
filtrationthe reaction mixture was filtered through a syringe
filtrationfilter
concentrationconcentrated
dissolutiondissolved in DMSO/MeOH (1:1, 0.8 mL)
customPurification via reverse phase

Sources & evidence

ORD record: ord-51674477503c48b092108e41785e6756
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309587B2

Reaction notes

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