Hydrochloric Acid → HCID 88138807, compound

HRID 617368Notes

Reaction equation

HRID 617368 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=1)(OC(C)(C)C)=O.[ClH:23]>C(O)C>[ClH:22].[ClH:23].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18391703HCID 18391703, compound

Product 1

HCID 88138807HCID 88138807, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 124 mg (0.40 mmol) of the compound from step 104a above in 3 mL of ethanol was added 10 mL of satd HCl in ethanol, and the reaction mixture was stirred for 1 hour at room temperature. The volatiles were removed under vacuum, and the residue was acidified and extracted with methylene chloride. The aqueous solution was made basic and extracted with methylene chloride. The extract was dried over MgSO4 and concentrated. The residue was purified on a column of silica gel, eluting with 10970 methanol in methylene chloride. The compound was converted to the salt by the HCl in ether according to Example 14c to afford the title compound. MS (DCI/NH3) m/e: 227 (M+H)+. 1H NMR (D2O, 300MHz) δ: 1.69-1.85 (m, 1H), 1.91-2.18 (m, 2H), 2.21-2.37 (m, 3H), 3.23-3.43 (m, 2H), 3.67-3.81 (m, 1H), 4.15-4.46 (m, 2H), 7.47 (m, 2H), 8.06 (d, J=3.5 Hz, 1H). Anal. Calc. for C11H15N2OCl.2 HCl: C, 45.09; H, 5.71; N, 9.34; Found C, 45.04; H, 6.01; N, 9.05. [α]25D =+19.00° (c=0.15, H2O).

Workup

  1. customThe volatiles were removed under vacuum
  2. extractionextracted with methylene chloride
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on a column of silica gel
  7. washeluting with 10970 methanol in methylene chloride

Sources & evidence

ORD record
ord-715bd04d968c4fa4961765f7fe63d1f1
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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