Thioglycolic Acid → 4-(4-Chloro-2-methyl-phenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one

HRID 1748762Notes

Reaction equation

[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:3]1.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[C:17]([CH3:23])[CH:16]=1.[C:24](O)(=[O:27])[CH2:25][SH:26]>C(#N)C>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[S:26][CH2:25][C:24](=[O:27])[NH:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[C:5]2=3)=[C:17]([CH3:23])[CH:16]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-methyl-5-(2-pyridyl)pyrazol-3-amine (1.1 g, 6.3 mmol, Example #2, step B), 4-chloro-2-methylbenzaldehyde (1.0 g, 6.5 mmol, Fluorochem), and thioglycolic acid (2.4 g, 26 mmol) in acetonitrile (20 mL) was heated, in a sealed microwave vessel, for about 20 min, at about 150° C., in a microwave. After cooling to rt the precipitated solid was collected by filtration and washed with acetonitrile (2 mL) to afford 4-(4-chloro-2-methyl-phenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one (1.16 g, 3.0 mmol, 48%), which was used as such: 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.50 (3 H, s); 3.07 (1 H, d, J=12 Hz); 3.50 (1 H, d, J=12 Hz); 3.84 (3 H, s); 6.59 (1 H, s); 6.86 (1 H, d, J=8 Hz); 6.98 (1 H, m); 7.1-7.2 (2 H, m); 7.68 (1 H, m), 7.76 (1 H, d, J=6 Hz); 8.4 (1 H, s); 10.2 (1 H, s).

Workup

temperatureAfter cooling to rt the precipitated solid
filtrationwas collected by filtration
washwashed with acetonitrile (2 mL)

Sources & evidence

ORD record: ord-be0d4c65fe81434bab87f040d12010bc
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150592B2

Reaction notes

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