Hydrochloric Acid → HCID 178487686, compound

HRID 2242449Notes

Reaction equation

HRID 2242449 reaction equation
C(O[K])CCC.[C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[NH:18][C:19]([C:21]1[N:22]=[C:23]([NH:26][CH:27]([CH3:29])[CH3:28])[S:24][CH:25]=1)=O)(=[O:9])[CH3:8].[ClH:30]>C(O)CCC>[ClH:30].[CH:27]([NH:26][C:23]1[S:24][CH:25]=[C:21]([C:19]2[CH:8]=[C:7]([OH:9])[C:10]3[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[N:18]=2)[N:22]=1)([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11953491N-(2-Acetyl-5-methoxyphenyl)-2-((1-methylethyl)amino)-4-thiazolecarboxamideHCID 178454393potassium butan-1-olate

Product 2

HCID 313Hydrochloric AcidHCID 178487686HCID 178487686, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of t.BuOK (2.42 g, 21 mmol) in anhydrous t.BuOH (40 mL) was heated to reflux. Compound 70 (1.8 g, 5.4 mmol) was added portion-wise over a 5 min period, and the dark red solution formed was stirred at reflux for an additional 20 min. The mixture was cooled to rt, and HCl (4 M in dioxane, 8.0 mL, 32 mmol) was added, after which the reaction mixture was concentrated under vacuum. In order to assure that all of the HCl and dioxane were removed, the crude product was re-dissolved in CH2Cl2 twice and thoroughly evaporated to obtain the slightly impure HCl salt of compound 71 (1.62 g) as a brown solid. The product was dissolved in CH2Cl2 and washed with saturated NaHCO3, after which the aqueous phase was extracted several times with CH2Cl2. The combined organic phases were dried (MgSO4) and evaporated to give compound 71 (1.38 g, 81%) as a light brown solid (>95% pure according to HPLC tests). 1H-NMR (MeOH-d4, 400 MHz): δ 1.30 (d, J=6.0 Hz, 6H), 3.93 (s, 3H), 3.95-4.07 (m, 1H), 6.73 (s, 1H), 6.99 (dd, J=2.4, 9.2 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.37 (s, 1H), 8.10 (d, J=9.2 Hz, 1H).

Workup

  1. customthe dark red solution formed
  2. temperatureat reflux for an additional 20 min
  3. concentrationafter which the reaction mixture was concentrated under vacuum
  4. customwere removed
  5. dissolutionthe crude product was re-dissolved in CH2Cl2 twice
  6. customthoroughly evaporated

Sources & evidence

ORD record
ord-0567cf24146c49869bb2047c6d8a36c3
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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