Hydrochloric Acid → HCID 60036677, compound

HRID 1948958Notes

Reaction equation

HRID 1948958 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([F:40])=[C:6]([CH:37]=[CH:38][CH:39]=1)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:35][CH3:36])=[C:15]([O:18][C@H:19]3[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]([O:33]C)=[O:32])[CH2:20]3)[CH:16]=2)[N:11]=[CH:10][N:9]=1.Cl>CO.C1COCC1.O>[Cl:3][C:4]1[C:5]([F:40])=[C:6]([CH:37]=[CH:38][CH:39]=1)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:35][CH3:36])=[C:15]([O:18][C@H:19]3[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]([OH:33])=[O:32])[CH2:20]3)[CH:16]=2)[N:11]=[CH:10][N:9]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 60036685HCID 60036685, compound

Product 1

HCID 60036677HCID 60036677, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (2M, 1.0 ml) was added to a stirred solution of 4-(3-chloro-2-fluoroanilino)-6-[(2S,4R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)pyrrolidin-4-yloxy]-7-methoxyquinazoline (prepared as described in Example 46; preparation of starting materials) in methanol (8 ml) and THF (3 ml) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was then reduced under vacuum and the residue dissolved in water and adjusted to pH 6 by the addition of hydrochloric acid (2N). The product was extracted with ethylacetate/n-propanol and the organic layer was washed with brine, dried over MgSO4 and the solvent removed under vacuum to give 4-(3-chloro-2-fluoroanilino)-6-[(2S,4R)-1-(tert-butoxycarbonyl)-2-carboxypyrrolidin-4-yloxy]-7-methoxyquinazoline as a white powder solid (0.42 g); Mass Spectrum: (M+H)+ 532.98

Workup

  1. extractionThe product was extracted with ethylacetate/n-propanol
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-fcdb8e6e7fc5496b8b19109ff7e131c2
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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