Hydrochloric Acid → HCID 21865233, compound

HRID 857666Notes

Reaction equation

HRID 857666 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[C:22]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[C:32]([NH2:35])[CH:31]=[CH:30]3)[N:21]=[CH:20][N:19]=1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]1[N:19]=[CH:20][N:21]=[C:22]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[C:32]([NH2:35])[CH:31]=[CH:30]3)[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58759705HCID 58759705, compound

Product 1

HCID 21865233HCID 21865233, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To {2-[6-(2-amino-quinolin-8-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester, (Example 148), (0.10 g, 0.20 mmol) was added 4 M HCl in dioxane (15 mL). The reaction mixture was stirred for 16 h and then concentrated in vacuum. The residue was dissolved in EtOAc (20 mL) and washed with NaHCO3 (2×50 mL), dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (2:1, EtOAc: hexanes) afforded the title compound as thick yellow oil. Mp: 233–234° C. MS (ESI, pos. ion) m/z: 398 (M+1).

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue was dissolved in EtOAc (20 mL)
  3. washwashed with NaHCO3 (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customPurification by silica gel chromatography (2:1, EtOAc: hexanes)

Sources & evidence

ORD record
ord-4a1cbf2740e8479a8604deee29e81454
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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