HCID 58746846, compound → HCID 21879441, compound

HRID 724649Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:31])[CH2:25]3)=[CH:20][CH:19]=2)[CH2:15][CH2:14][C:13](=[O:16])[NH:12]1)=O>C(O)(=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C:11]1([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:31])[CH2:25]3)=[CH:20][CH:19]=2)[CH2:15][CH2:14][C:13](=[O:16])[NH:12]1

Participants

Conditions

Temperature: 120 °C

Procedure

N-(2-aminophenyl)-2-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]-5-oxopyrrolidine-2-carboxamide (6.6 mg, 0.01 mmol) was stirred in acetic acid (0.5 mL) and heated to 120° C. for 60 seconds in a microwave. Purification by preparative LCMS gave the title compound as a white solid, (2.5 mg, 42%), 1H NMR (400 MHz, CD3OD): δ 7.80 (m, 2H), 7.62 (m, 2H), 7.50 (d, J=8.8 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H, 5.20 (m, 1H), 3.50 (m, 2H), 2.65 (m, 1H), 2.50 (m, 1H), 2.35 (m, 1H), 2.26 (m, 1H), 2.03 (m, 1H), 1.70 (m, 1H); LCMS found for C21H20N2O4S (M+H)+: m/z=425.

Workup

customPurification by preparative LCMS

Sources & evidence

ORD record: ord-30e60af23e0d43f59cf6e0a49a7866a7
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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