Phosphorus oxychloride → HCID 57742798, compound

HRID 335211Notes

Reaction equation

HRID 335211 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:21])=O)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]#[N:21])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 57742603HCID 57742603, compound

Product 1

HCID 57742798HCID 57742798, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

3-(5-Bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)benzamide (0.20 g, 0.48 mmol) was suspended in acetonitrile (4 mL). POCl3 (0.11 mL, 1.2 mmol) was added and the reaction stirred in a sealed tube at 70° C. for 4 hours. The solution was cooled and neutralized with saturated NaHCO3 solution. The material was extracted with EtOAc, dried, and concentrated. The crude material was triturated with ether/EtOAc and filtered. The solid was dried to give the title compound (0.065 g, 34%). 1H NMR (DMSO-d6) δ 2.17 (s, 3H), 6.44 (bs, 1H), 7.58-7.68 (m, 3H), 7.83 (d, 1H), 7.92 (s, 1H), 8.36 (s, 1H).

Workup

  1. temperatureThe solution was cooled
  2. extractionThe material was extracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was triturated with ether/EtOAc
  6. filtrationfiltered
  7. customThe solid was dried

Sources & evidence

ORD record
ord-a80c8a27a3724b2e984c214e48e51869
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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