Pyridine → HCID 178452652, compound

HRID 2110278Notes

Reaction equation

HRID 2110278 reaction equation
N[C:2]1[C:10]2[C:5](=[C:6]([F:26])[C:7]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:13]([F:25])[CH:12]=3)=[CH:8][CH:9]=2)[NH:4][N:3]=1.[S:27]1[CH:31]=[CH:30][C:29]([C:32](Cl)=[O:33])=[CH:28]1.[N:35]1C=CC=CC=1>>[F:26][C:6]1[C:7]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])=[C:13]([F:25])[CH:12]=2)=[CH:8][CH:9]=[C:10]2[C:5]=1[NH:4][N:3]=[C:2]2[C:28]1[S:27][CH:31]=[CH:30][C:29]=1[C:32]([NH2:35])=[O:33]

Participants

4

Reactant 3

HCID 1049PyridineHCID 27763773-Thenoyl chlorideHCID 86760856HCID 86760856, compound

Product 1

HCID 178452652HCID 178452652, compound

Procedure

A solution of 1.5 g of tert-butyl [4-(3-amino-7-fluoro-1H-indazol-6-yl)-2-fluoro -phenyl]carbamate in 34 mL of pyridine is admixed at 15° C. with 0.61 g of thiophene-3-carbonyl chloride. The reaction mixture is stirred for 18 h and then poured into distilled water and extracted with ethyl acetate. The organic phase is washed a number of times with distilled water and then with saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated to dryness under reduced pressure. This gives 1.58 g of (7-fluoro-6-{3-fluoro-4-tert-butyloxycarbonylaminophenyl}-1H-indazol-3-yl)thiophene-3-carboxamide in the form of a cream-colored solid, whose characteristics are as follows:

Workup

  1. additionpoured
  2. distillationinto distilled water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed a number of times with distilled water
  5. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b760f01879d5465f82e6187d08ea140d
Source dataset
uspto-grants-2009_04
Patent number
US07517902B2

Reaction notes

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