Hydrochloric Acid → HCID 21093943, compound

HRID 729735Notes

Reaction equation

HRID 729735 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([CH:16]([CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:17]([NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:18])[CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13].[ClH:32]>O>[Cl:32][C:6]1[CH:7]=[C:8]([CH:16]([CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:17]([NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:18])[CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21093939HCID 21093939, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21093943HCID 21093943, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaNO2 (34 mg, 498 μmol) in H2O (0.8 mL) was added to a solution of 2-(3-amino-4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 171, 200 mg, 488 μmol) in 6M HCl (1.6 mL) at 0° C. The reaction was stirred at 0° C. for 35 min, before being added slowly to a stirred mixture of Cu powder (80 mg, 1.26 mmol) and 12M HCl (0.8 mL) at 0° C. The temperature was increased to 20° C., then stirring was continued for 1 h. The mixture was then heated at 60° C. for 1 h, before being cooled down to 20° C. and extracted with CH2Cl2 (3×15 mL). The organic extracts were dried (MgSO4), filtered, and concentrated to give a residue that was purified by RP-HPLC to furnish the title compound: RTA=3.17 min; m/z (ES+)=429.2 [M+H]+.

Workup

  1. temperatureThe temperature was increased to 20° C.
  2. stirringstirring
  3. waitwas continued for 1 h
  4. temperatureThe mixture was then heated at 60° C. for 1 h
  5. temperaturebefore being cooled down to 20° C.
  6. extractionextracted with CH2Cl2 (3×15 mL)
  7. dry with materialThe organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a residue that
  11. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-3164adae5207451d8255bb732be893e9
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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