Sodium Hydroxide → HCID 58746424, compound

HRID 723963Notes

Reaction equation

HRID 723963 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:35]=[CH:34][C:16]2[N:17]=[C:18]([NH:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[S:19][C:15]=2[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[CH2:27]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:18]2[S:19][C:15]3[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:35]=[CH:34][C:16]=3[N:17]=2)[CH2:22][CH2:23]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58746426HCID 58746426, compound

Product 1

HCID 58746424HCID 58746424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzoyl-3-[2-(1-benzyl-piperidin-4-ylamino)-benzothiazol-6-yl]-thiourea (Example 37, 29 mg, 0.058 mmol) was placed in an argon purged flask. THF (3 mL) was added followed by 2M NaOH (0.13 mL, 4.4 eq.). The mixture was heated to reflux for 44 hours. The solvent was evaporated. The mixture was diluted with water (2 mL) and ethyl acetate (10 mL). The layers were separated and the aqueous phase (saturated with NaCl) extracted with ethyl acetate (2×10 mL). The combined organic fractions were dried over MgSO4, filtered and evaporated to give a yellow oil which was dried under high vacuum overnight. (crude yield: 25.2 mg). The product was used directly in the subsequent step (Example 39).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 44 hours
  3. customThe solvent was evaporated
  4. additionThe mixture was diluted with water (2 mL) and ethyl acetate (10 mL)
  5. customThe layers were separated
  6. extractionthe aqueous phase (saturated with NaCl) extracted with ethyl acetate (2×10 mL)
  7. dry with materialThe combined organic fractions were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give a yellow oil which
  11. customwas dried under high vacuum overnight

Sources & evidence

ORD record
ord-4d6fe71f476e4f9e9b95fed5ea016f30
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

Loading…