Sulfuric Acid → HCID 58094973, compound

HRID 2282313Notes

Reaction equation

HRID 2282313 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:8]=2)=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23].[C:24](OC(=O)C)(=[O:26])[CH3:25].S(=O)(=O)(O)O>>[C:24]([NH:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:8]=2)=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])(=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 58094789HCID 58094789, compound

Product 1

HCID 58094973HCID 58094973, compoundYield 62.4%

Procedure

To a stirred solution of N-{4-[5-amino-4-(2-chlorophenyl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide (0.020 g, 0.058 mmol) in anhydrous acetic anhydride (1.00 mL, 10.60 mmol) was added dropwise concentrated sulfuric acid (0.002 mL, 0.030 mmol) and stirred for 18 h. The reaction was quenched by the dropwise addition of a triethylamine (0.200 mL) and concentrated in vacuo. The residue was purified by column chromatography (SiO2, elution with 0-100% EtOAc in hexanes) to provide 0.014 g of product as a yellow oil (62%). LC/MS (AA) ES+ 387, 389. 1H NMR (400 MHz, d1 CDCl3) δ: 9.10 (br s, 1H), 8.63 (br s, 1H), 8.31-8.30 (m, 0.5H), 7.64-7.24 (m, 6.5H), 2.18 (s, 3H), 2.14 (s, 3H).

Workup

  1. customThe reaction was quenched by the dropwise addition of a triethylamine (0.200 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2, elution with 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-09d459676b774f8dbef7b4eccde8016c
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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