Hydrochloric Acid → HCID 19745802, compound

HRID 2253579Notes

Reaction equation

HRID 2253579 reaction equation
C([O:3][C:4]([NH:6][C:7]([CH2:27][CH3:28])=[CH:8][C:9]([NH:11][C:12]1[C:13]([F:26])=[CH:14][C:15]2[O:20][CH2:19][C:18](=[O:21])[N:17]([CH2:22][C:23]#[CH:24])[C:16]=2[CH:25]=1)=[O:10])=O)C.C[O-].[Na+].Cl>CO.O>[CH2:27]([C:7]1[NH:6][C:4](=[O:3])[N:11]([C:12]2[C:13]([F:26])=[CH:14][C:15]3[O:20][CH2:19][C:18](=[O:21])[N:17]([CH2:22][C:23]#[CH:24])[C:16]=3[CH:25]=2)[C:9](=[O:10])[CH:8]=1)[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 53693446HCID 53693446, compound

Product 1

HCID 19745802HCID 19745802, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
62 °C

Procedure

A suspension of 6.45 g of 6-[3-(ethoxycarbonylamino)-2-pentenoylamino]-3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine and 3.22 g of sodium methylate in 6.5 ml of methanol is stirred at 62° C. for 4 hours. The solution which thus results is left to stand at room temperature for 64 hours and subsequently poured into a solution of 15 ml of 2N hydrochloric acid in 400 ml of water. The resulting precipitate is filtered off under suction, washed with water and recrystallized from acetone/n-hexane. In this manner there is obtained 6-ethyl-3-[3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-2,4(1H,3H)-pyrimidinedione, m.p. 240° C. (with decomposition).

Workup

  1. customThe solution which thus results
  2. waitis left
  3. waitto stand at room temperature for 64 hours
  4. filtrationThe resulting precipitate is filtered off under suction
  5. washwashed with water
  6. customrecrystallized from acetone/n-hexane

Sources & evidence

ORD record
ord-4f69566d5e834974831c94ba380ffe20
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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