2-Mercapto-2-methylpropanoic acid → HCID 136348449, compound

HRID 1748782Notes

Reaction equation

[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[N:6]([CH3:10])[N:5]=2)[CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[C:14]([CH3:20])[CH:13]=1.[SH:21][C:22]([CH3:27])([CH3:26])[C:23](O)=[O:24]>C(#N)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[S:21][C:22]([CH3:27])([CH3:26])[C:23](=[O:24])[NH:9][C:7]3[N:6]([CH3:10])[N:5]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[C:8]2=3)=[C:14]([CH3:20])[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine (3 g, 22 mmol, Fluorochem), 4-chloro-2-methylbenzaldehyde (3.1 g, 22 mmol, Fluorochem), and 2-mercapto-2-methylpropanoic acid (3.5 g, 33 mmol, Chemwish) was heated, in a sealed microwave vessel, for about 60 min, at about 80° C. Subsequently, the reaction mixture was heated, for about 24 h, at about 150° C. After cooling to rt, acetonitrile (20 mL) was added and the reaction mixture was stirred for about 2 h, at about 40° C. After cooling to about 0° C., the precipitated solid was collected by filtration and washed with acetonitrile (2 mL) to afford 4-(4-chloro-2-methyl-phenyl)-3-cyclopropyl-1,6,6-trimethyl-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one as white solid (1.25 g, 3.3 mmol, 15%). 1H-NMR (CDCl3, Bruker 400 MHz) δ 0.30-0.39 (1H, s); 0.46-0.67 (3H, m); 0.83-0.93 (1H, m); 1.50 (3H, s); 1.66 (3H, s); 2.48 (3H, s); 3.75 (3H, s); 5.58 (1H, s); 7.09 (1H, dd, J=8.5, 2.5 Hz); 7.14 (1H, d, J=2.5 Hz); 7.21 (1H, d, J=8.5 Hz); H, m); 8.65 (1H, s).

Workup

temperatureSubsequently, the reaction mixture was heated, for about 24 h, at about 150° C
temperatureAfter cooling to rt
temperatureAfter cooling to about 0° C.
filtrationthe precipitated solid was collected by filtration
washwashed with acetonitrile (2 mL)

Sources & evidence

ORD record: ord-500e611e4d644b09828b3f7112b4004f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150592B2

Reaction notes

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