Sodium Hydroxide → HCID 58838517, compound

HRID 2374454Notes

Reaction equation

HRID 2374454 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:11]([NH:14][C:15]2[N:20]=[C:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[C:17]([CH3:29])[CH:16]=2)(=[O:13])=[O:12])=[C:8]([CH3:10])[N:9]=1)(=O)C.[OH-].[Na+]>CO>[NH2:4][C:5]1[S:6][C:7]([S:11]([NH:14][C:15]2[N:20]=[C:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:18]=[C:17]([CH3:29])[CH:16]=2)(=[O:13])=[O:12])=[C:8]([CH3:10])[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58838513HCID 58838513, compound

Product 1

HCID 58838517HCID 58838517, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
24 °C

Procedure

A solution of tert-butyl [6-({[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]sulfonyl}amino)-4-methylpyridin-2-yl]carbamate (2.1 g, 4.8 mmol, 1 equiv) and 1 N aqueous sodium hydroxide (7.2 mL) in methanol (30 mL) was heated to 50° C. for 48 h. Upon cooling to 24° C., the reaction mixture was concentrated in vacuo (˜25 mm Hg). The resulting solid was dissolved in water (20 mL). The solution was neutralized with concentrated hydrochloric acid until pH=7. The resulting solid was collected by filtration, washed with water (30 mL) and diethyl ether (2×30 mL) (1.59 g, 83%). 1H NMR (400 MHz, CDCl3), δ: 8.29 (br s, 1H), 7.48 (s, 1H), 6.91 (s, 1H), 2.40 (s, 3H), 2.33 (s, 3H), 1.52 (s, 9H); LCMS (ESI) m/z: 400.2.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo (˜25 mm Hg)
  2. dissolutionThe resulting solid was dissolved in water (20 mL)
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water (30 mL) and diethyl ether (2×30 mL) (1.59 g, 83%)

Sources & evidence

ORD record
ord-f3c089309bf24e908309797ec2e19a30
Source dataset
uspto-grants-2008_12
Patent number
US07462634B2

Reaction notes

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