Diisopropylethylamine → HCID 71621788, compound

HRID 871019Notes

Reaction equation

HRID 871019 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[C:3]=1[C:14]([NH2:16])=[O:15].C(N(CC)C(C)C)(C)C.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=1[N:34]=[C:35]=[O:36]>O1CCOCC1>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:35]([NH:34][C:28]3[CH:29]=[C:30]([CH3:33])[CH:31]=[CH:32][C:27]=3[F:26])=[O:36])=[CH:11][CH:12]=2)[C:3]=1[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27333772-Fluoro-5-methylphenyl isocyanateHCID 71621924HCID 71621924, compound

Product 1

HCID 71621788HCID 71621788, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-amino-3-(4-aminophenyl)isothiazole-4-carboxamide (18 mg, 0.079 mmol), N,N-diisopropylethylamine (0.034 mL, 0.20 mmol), and 2-fluoro-5-methylphenyl isocyanate (0.014 mL, 0.11 mmol) in 1.0 mL dioxane was reacted at room temperature for 2.5 hours. The reaction was quenched with 0.5 mL MeOH, stirred 5 min at room temperature, and then evaporated. The residue was recrystallized from EtOAc/CHCl3 to give the title compound as a pale yellow solid (27 mg, 88%).

Workup

  1. customwas reacted at room temperature for 2.5 hours
  2. customThe reaction was quenched with 0.5 mL MeOH
  3. customevaporated
  4. customThe residue was recrystallized from EtOAc/CHCl3

Sources & evidence

ORD record
ord-f980e2a4ebc54afb948b8f109b334d08
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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