Hydrochloric Acid → HCID 67280447, compound

HRID 1693312Notes

Reaction equation

HRID 1693312 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([CH2:19][C:20]([O:22]C)=[O:21])[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([CH2:19][C:20]([OH:22])=[O:21])[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86641343HCID 86641343, compound

Product 1

HCID 67280447HCID 67280447, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture composed of methyl {4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}acetate of Example 111 (218 mg), methanol (8 ml) and a 1 N sodium hydroxide solution (0.22 ml) was stirred at room temperature for eight hours. A 1 N hydrochloric acid solution (2.5 ml) was added dropwise to the reaction mixture under ice-cooling, and methanol in the reaction mixture was evaporated under reduced pressure. A 0.5 N hydrochloric acid solution was added to the resulting residue, followed by extraction with chloroform. The organic layer was concentrated to dryness under reduced pressure to obtain the title compound (173 mg, 97%) as an amorphous.

Workup

  1. temperaturecooling
  2. custommethanol in the reaction mixture was evaporated under reduced pressure
  3. additionA 0.5 N hydrochloric acid solution was added to the resulting residue
  4. extractionfollowed by extraction with chloroform
  5. concentrationThe organic layer was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-741e4fa949314e27b8776c902288023f
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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