HCID 53627652, compound → HCID 53627661, compound

HRID 1696163Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of (S)-4-(3-(indolin-1-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)-benzenesulfonamide (10 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-(1H-Indol-1-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide. 1H NMR (400 MHz, DMSO-d6) δ 7.84 (d, J=2.1 Hz, 2H), 7.82 (d, J=3.0 Hz, 2H), 7.47 (d, J=7.9 Hz, 1H), 7.29 (d, J=7.9 Hz, 1H), 7.19 (d, J=3.3 Hz, 1H), 7.08-7.03 (m, 1H), 7.01-6.94 (m, 2H), 6.62 (d, J=4.7 Hz, 1H), 6.44 (d, J=3.2 Hz, 1H), 5.51 (dd, J=8.9, 10.9 Hz, 1H), 4.02-3.98 (m, 2H), 2.72-2.68 (m, 1H), 2.49-2.40 (m, 1H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=439.2; tR=2.99 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-375de6b89deb470a81a3222c9857e7db
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163720B2

Reaction notes

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