5-Aminoindole → 2-Butyl-4-(1H-indol-5-ylamino)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729293Notes

Reaction equation

[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].[NH:20]1[C:28]2[C:23](=[CH:24][C:25]([NH2:29])=[CH:26][CH:27]=2)[CH:22]=[CH:21]1>CN(C=O)C>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:29][C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[NH:20][CH:21]=[CH:22]3)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (110 mg, 0.330 mmol) was dissolved in dry DMF (0.5 mL) under nitrogen atmosphere. 1H-Indol-5-amine (131 mg, 0.991 mmol) was added and the reaction mixture was heated in a microwave reactor at 140° C. for 25 mins. The crude product was purified by preparative HPLC affording the title compound (126 mg, 96.5%). 1H NMR (500 MHz, CD3CN): δ 1.01 (t, 3H), 1.44-1.53 (m, 2H), 1.78-1.86 (m, 2H), 3.75 (t, 2H), 6.20-6.22 (m, 1H), 6.68-6.71 (m, 1H), 6.99-7.18 (m, 8H), 7.76 (bs, 1H), 9.18 (bs, 1H).

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-73301130fd684dcab37ebf0c4b330da1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582629B2

Reaction notes

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