Hydrochloric Acid → HCID 178456286, compound

HRID 902183Notes

Reaction equation

HRID 902183 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[C:22]#[N:23])[N:15]([CH2:24][C:25]3[CH:29]=[C:28]([C:30]4[S:31][C:32](Cl)=[CH:33][CH:34]=4)[O:27][N:26]=3)[N:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[NH2:36][OH:37].[ClH:38].CC([O-])(C)C.[K+]>CO>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[C:22](=[NH:23])[NH:36][OH:37])[N:15]([CH2:24][C:25]3[CH:29]=[C:28]([C:30]4[S:31][C:32]([Cl:38])=[CH:33][CH:34]=4)[O:27][N:26]=3)[N:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 23665647Potassium tert-butoxideHCID 86760648HCID 86760648, compound

Product 1

HCID 178456286HCID 178456286, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 200 mg 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-cyano-1H-indazole-3-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide in 3 mL methanol, 27 mg NH2OH*HCl and 44 mg KOt-Bu were added and the mixture was heated to 50° C. for 3 d. After cooling to RT the precipitated inorganic salts were filtered off. The precipitate was washed with methanol (2×5 ml) and the combined filtrates were collected and concentrated under reduced pressure. The residue was subjected to the next reaction step without further purification. Yield: 223 mg.

Workup

  1. additionwere added
  2. temperatureAfter cooling to RT the precipitated inorganic salts
  3. filtrationwere filtered off
  4. washThe precipitate was washed with methanol (2×5 ml)
  5. customthe combined filtrates were collected
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-1535851f94124976a944885718b4f1a3
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Reaction notes

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