Acetic Anhydride → HCID 24826052, compound

HRID 1514363Notes

Reaction equation

HRID 1514363 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([N:15]3[CH:23]=[C:22]4[C:17]([CH:18]=[C:19]([N+:24]([O-])=O)[CH:20]=[CH:21]4)=[N:16]3)[N:10]=2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([N:15]3[CH:23]=[C:22]4[C:17]([CH:18]=[C:19]([NH:24][C:27](=[O:29])[CH3:28])[CH:20]=[CH:21]4)=[N:16]3)[N:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 24825962HCID 24825962, compound

Product 1

HCID 24826052HCID 24826052, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

(4-Chloro-phenyl)-[2-(6-nitro-indazol-2-yl)-pyrimidin-4-yl]-amine (500 mg, 1.36 mmol) and iron powder (152 mg, 2.73 mmol) was suspended in acetic anhydride (10 mL) and acetic acid (10 mL). The reaction mixture was heated to 100° C. over night and concentrated in vacuo. Water (30 mL) was added followed by extraction with chloroform (3×30 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulphate, filtrated and concentrated in vacuo to give the crude product as a brown solid. Preparative HPLC gave N-{2-[4-(4-chloro-phenylamino)-pyrimidin-2-yl]-2H-indazol-6-yl}-acetamide (35.2 mg, 6%) as a purple solid. LC-ESI-HRMS of [M+H]+ shows 379.1073 Da. Calc. 379.107412 Da, dev. −0.3 ppm.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (30 mL) was added
  3. extractionfollowed by extraction with chloroform (3×30 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. customto give the crude product as a brown solid

Sources & evidence

ORD record
ord-2a113d883c9f4163930efa177b8dc115
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

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