5-methyl-1-phenyl-1H-pyrazol-3-amine → HCID 11690667, compound

HRID 729303Notes

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].[CH3:20][C:21]1[N:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:24]=[C:23]([NH2:32])[CH:22]=1>CN(C=O)C>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:32][C:23]2[CH:22]=[C:21]([CH3:20])[N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:24]=2)=[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. 5-Methyl-1-phenyl-1H-pyrazol-3-amine (172 mg, 0.991 mmol) was added and the reaction mixture was heated in a microwave reactor for 25 mins at 140° C. The crude product was purified by preparative HPLC affording the title compound (89 mg, 58.6%). 1H NMR (500 MHz, CD3CN): δ 0.99 (t, 3H), 1.42-1.51 (m, 2H), 1.76-1.84 (m, 2H), 2.14 (s, 3H), 3.73 (t, 2H), 5.87 (s, 1H), 6.87-6.90 (m, 2H), 7.27-7.38 (m, 8H), 7.74 (bs, 1H).

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-69c6d3314c8b4974a4d6e5641c9d7b67
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582629B2

Reaction notes

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