Acetic Acid → HCID 135531244, compound

HRID 601099Notes

Reaction equation

HRID 601099 reaction equation
[CH2:1]([N:5]1[C:10]2[N:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])O[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].[O:17]=[S:18]1(=[O:34])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][C:20]([CH2:28]C(OCC)=O)=[N:19]1.[H-].[Na+].C(O)(=O)C>C1COCC1.Cl>[CH2:1]([N:5]1[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]([OH:15])=[C:28]([C:20]2[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:18](=[O:34])(=[O:17])[N:19]=2)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 6588352H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxideHCID 103985421-butyl-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione

Product 1

HCID 135531244HCID 135531244, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product of Example 1B (0.220 g, 1.0 mmol) and the product of EXAMPLE 1C (0.268 g, 1.0 mmol) in anhydrous THF (10 mL) under nitrogen at 0° C. was added sodium hydride (95%, 0.10 g, 4.0 mmol). The reaction was heated to reflux for 3 hours, cooled to 0° C., and to it was added dropwise glacial acetic acid (2 mL). The resulting mixture was heated to reflux for 2 hours, cooled to ambient temperature, and diluted with aqueous hydrochloric acid (0.1 M, 10 mL). The resulting precipitate was collected by filtration, washed with water and diethyl ether and dried to give the title compound (0.130 g, 33%). MS (ESI−) m/z 397 (M−H)−.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux for 2 hours
  5. temperaturecooled to ambient temperature
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-c395f635f38f47a995f26ed631b2d125
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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