HCID 67335596, compound → HCID 67335638, compound

HRID 1672159Notes

Reaction equation

HRID 1672159 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][CH2:7][C:8]1([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)C>Cl>[NH:20]1[C:21]2[C:17](=[CH:16][C:15]([N:14]3[C:8]4([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]4)[CH2:7][NH:6][CH2:5][C:4]3=[O:3])=[CH:23][CH:22]=2)[CH:18]=[N:19]1

Participants

3

Reactant 1

HCID 67335596HCID 67335596, compound

Product 1

HCID 67335638HCID 67335638, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of {[1-(1H-indazol-5-ylamino)-cyclohexylmethyl]-amino}-acetic acid ethyl ester (0.808 g, 2.45 mmol) in 2N HCl (11 mL) was heated at reflux for 17 hours, then cooled to room temperature and quenched by the careful addition of K2CO3 until no more effervescence was observed. The resulting mixture was extracted with DCM and the combined extracts were dried (MgSO4), filtered and concentrated in vacuo to furnish 1-(1H-indazol-5-yl)-1,4-diaza-spiro[5.5]undecan-2-one (0.350 g, 1.23 mmol, 50%) as a solid that was used directly without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. customquenched by the careful addition of K2CO3 until no more effervescence
  4. extractionThe resulting mixture was extracted with DCM
  5. dry with materialthe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e4b7f83f7704762aa2c547187b91f43
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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