Acetic Acid → HCID 178524307, compound

HRID 1827480Notes

Reaction equation

HRID 1827480 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([N:18](COCC[Si](C)(C)C)[C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21]([OH:23])=[O:22])=[CH:15][CH:16]=2)[NH:11][N:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C(N)CN.C(O)(=O)C>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21]([OH:23])=[O:22])=[CH:15][CH:16]=2)[NH:11][N:10]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 178504266HCID 178504266, compound

Product 1

HCID 178524307HCID 178524307, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-[3-Pyridin-2-ylethynyl- -(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamino]-benzoic acid (231 mg, 0.477), 1M tetrabutylammonium fluoride in THF (3.8 mL, 3.816 mmol), and ethylenediamine (127 μL, 1.908 mmol), were stirred in an oil bath at 80 deg C. for 6 h. The reaction was quenched with acetic acid (218 μL, 3.816 mmol), diluted with water, and extracted with EtOAc (10×50 mL). The combined organics were washed with brine and dried over MgSO4. After concentrating a solid forms which was triturated with CH2Cl2, giving the product as a yellow powder (124 mg, 73%). ESIMS M−H−): 353.0.

Workup

  1. extractionextracted with EtOAc (10×50 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentrating a solid forms which
  5. customwas triturated with CH2Cl2

Sources & evidence

ORD record
ord-b56bfdd33cd6448f9a8239cb3e7c8c86
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

Loading…