Hydrochloric Acid → HCID 59110534, compound

HRID 479685Notes

Reaction equation

HRID 479685 reaction equation
[OH:1][CH2:2][CH:3]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]([NH:26][C:27]2[N:28]=[C:29]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)[S:30][CH:31]=2)=[O:25])[N:18]=1)C(=O)OC(C)(C)C)[CH2:4][CH:5]([CH3:7])[CH3:6].Cl.[OH-].[Na+]>CO>[OH:1][CH2:2][CH:3]([NH:8][CH2:16][C:17]1[N:18]=[C:19]([NH:23][C:24]([NH:26][C:27]2[N:28]=[C:29]([C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)[S:30][CH:31]=2)=[O:25])[CH:20]=[CH:21][CH:22]=1)[CH2:4][CH:5]([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59110560HCID 59110560, compound

Product 1

HCID 59110534HCID 59110534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl (1-hydroxymethyl-3-methyl-butyl)-(6-[3-(2-pyridin-4-yl-thiazol-4-yl)-ureido]-pyridin-2-ylmethyl}-carbamate (165 mg, 0.313 mmol, Example 62) in MeOH (5 mL) was treated with HCl (0.16 mL, 0.627 mmol, 4M in dioxane). The resulting stirred solution was heated at 40° C. in a closed system for 15 h. After cooling to RT, the pH was adjusted to 7 using 1 N NaOH. Solvent was removed and the residue was extracted with CHCl3. The organic layer was washed with H2O, brine, dried over MgSO4, and concentrated to yield a brown liquid crude product. This crude product was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (95:5) gave the final compound as a tan solid. MS m/z: 427.2 (M+H). Calc'd. for C21H26N6O2S-426.54.

Workup

  1. temperatureAfter cooling to RT
  2. customSolvent was removed
  3. extractionthe residue was extracted with CHCl3
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto yield a brown liquid crude product
  8. customThis crude product was purified by chromatography on silica gel
  9. washElution with CH2Cl2

Sources & evidence

ORD record
ord-0d7f49afc96b4c7e9c356a736370e258
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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