2-Aminothiophenol → HCID 49869134, compound

HRID 570956Notes

Reaction equation

[CH3:1][O:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14](O)=O)=[C:7]2[N:6]=[N:5]1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>C(Cl)(Cl)Cl>[S:24]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:14]1[C:13]1[N:12]=[CH:11][N:8]2[C:9](=[O:10])[N:4]([CH2:3][O:2][CH3:1])[N:5]=[N:6][C:7]=12

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of polyphosphate ester (see, e.g., Yalpn et al., Eur. J. Med. Chem., 1992, Vol. 27, pp. 401-406) (1 g) and chloroform (3 mL) was added 3-(methoxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (225 mg; 1 mmol) and 2-aminothiophenol (107 μL; 1 mmol). The mixture was carefully heated to 70° C. for 3.5 hours, then cooled and the chloroform removed under reduced pressure. The residue was added to water (100 mL), which was extracted with ethyl acetate (×3). The combined organic fractions were dried (MgSO4) and concentrated. The crude product was washed with ether/hexane, and purified by column chromatography to give a pale yellow powder (0.007 g; 3%). δH (DMSO d6): 9.03 (1H, s), 8.22 (1H, d, J=7.9), 8.17 (1H, d, J=7.9), 7.61 (1H, td, J=7.7, 1.3), 7.53 (1H, td, J=7.6, 1.2), 5.65 (2H, s), 3.46 (3H, s).

Workup

temperaturecooled
customthe chloroform removed under reduced pressure
additionThe residue was added to water (100 mL), which
extractionwas extracted with ethyl acetate (×3)
dry with materialThe combined organic fractions were dried (MgSO4)
concentrationconcentrated
washThe crude product was washed with ether/hexane
custompurified by column chromatography
customto give a pale yellow powder (0.007 g; 3%)

Sources & evidence

ORD record: ord-ec71a18b6826473f8d12755b5442dbcf
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024018B2

Reaction notes

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