Hydrazine → HCID 178456809, compound

HRID 1452978Notes

Reaction equation

HRID 1452978 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][C:10]1[N:15]=[C:14]2[S:16][C:17]([NH:19][CH:20]([CH3:22])[CH3:21])=[N:18][C:13]2=[CH:12][CH:11]=1.NN.C[N:27]([CH:29]=O)C.CC([N:34](C)C)=O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:10]2[N:15]=[C:14]3[S:16][C:17]([NH:19][CH:20]([CH3:22])[CH3:21])=[N:18][C:13]3=[CH:12][CH:11]=2)=[CH:29][NH:27][N:34]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 22628260N,N-dimethylformamide N,N-dimethylacetamideHCID 57527199HCID 57527199, compound

Product 1

HCID 178456809HCID 178456809, compoundYield 29%

Procedure

A solution of 1-(2-fluorophenyl)-2-(2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)ethanone (0.0403 g, 0.122 mmol, 1.0 eq.) in DMF/DMA (1.0 mL) was heated under nitrogen at 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was concentrated in vacuo and dissolved in EtOH (0.5 mL). Hydrazine (0.1 mL, 3.19 mmol, 26.1 eq.) was added, and the reaction was allowed to stand for 2.75 hr and then concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give 5-(3-(2-fluorophenyl)-1H-pyrazol-4-yl)-N-isopropylthiazolo[5,4-b]pyridin-2-amine as a light yellow solid (0.0125-g, 29% yield). LC/MS (MH)=354.26.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOH (0.5 mL)
  3. concentrationconcentrated in vacuo
  4. additionMeOH was added to the residue
  5. customThe appropriate fractions were collected
  6. additionNaHCO3 (s) was added
  7. concentrationThe solution was then concentrated in vacuo not to dryness
  8. extractionextracted with CH2Cl2 (3×)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d70dbac853e14cf684ba1a17f168e801
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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