Diisopropylethylamine → HCID 178509315, compound

HRID 1663481Notes

Reaction equation

HRID 1663481 reaction equation
[NH2:1][C:2]1[C:3]([C:7](SC)=[N:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Br:16])[CH:10]=2)=[N:4][S:5][N:6]=1.Cl.[NH2:20][OH:21].C(N(CC)C(C)C)(C)C>C(O)C>[NH2:1][C:2]1[C:3]([C:7](=[N:20][OH:21])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Br:16])[CH:10]=2)=[N:4][S:5][N:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58558200Methyl 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbimidothioate

Product 1

HCID 178509315HCID 178509315, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of methyl 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbimidothioate (78 mg, 0.22 mmol) in ethanol (2.3 mL) was treated with hydroxylamine hydrochloride (62 mg, 0.9 mmol) followed by N,N-diisopropylethylamine (180 μL, 1.0 mmol) and stirred at 90° C. for 16 h. The reaction mixture was purified by preparative HPLC to give the desired product (58 mg, 78%). LCMS for C9H8BrFN5OS (M+H)+: m/z=331.9, 333.9.

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-fba01f8b3124431ab77a99be2f729de8
Source dataset
uspto-grants-2011_10
Patent number
US08034953B2

Reaction notes

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