Hydrochloric Acid → HCID 69311886, compound

HRID 2217903Notes

Reaction equation

HRID 2217903 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:15]=[CH:14][C:13]3[C:12]([C:16]([NH:18][CH2:19]C4CCCCC4)=[O:17])=[C:11]([Cl:26])[CH:10]=[CH:9][C:8]=3[N:7]=2)[CH2:3]1.[C:27]([O:31]CC)(=[O:30])[CH:28]=[CH2:29].[OH-].[Na+].Cl>CO>[Cl:26][C:11]1[C:12]([C:16]([NH:18][CH2:19][CH2:16][CH:12]2[CH2:13][CH2:8][CH2:9][CH2:10][CH2:11]2)=[O:17])=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([N:4]1[CH2:5][CH:2]([NH:1][CH2:29][CH2:28][C:27]([OH:31])=[O:30])[CH2:3]1)[CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 68808743HCID 68808743, compound

Product 1

HCID 69311886HCID 69311886, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(3-amino-1-azetidinyl)-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide (Example 97(a)) (0.1 g) in methanol (1 mL) was added ethyl acrylate (0.032 mL). The mixture was stirred at room temperature for 20 hours. Sodium hydroxide (1 mL, 1M) was added and the reaction mixture was stirred for 72 hours. Hydrochloric acid (0.5 mL, 2M) was added and the reaction mixture was concentrated under vacuum. Purification (HPLC—Symmetry, 0.1% aqueous ammonium acetate:acetonitrile as eluant) gave the title compound as a solid (0.026 g).

Workup

  1. stirringthe reaction mixture was stirred for 72 hours
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customPurification (HPLC—Symmetry, 0.1% aqueous ammonium acetate:acetonitrile as eluant)

Sources & evidence

ORD record
ord-c6af45f321b24766a072a2cfe15adf8c
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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