Trifluoroacetic acid → HCID 58466273, compound

HRID 335687Notes

Reaction equation

HRID 335687 reaction equation
C([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:30]=1)[C:22]1[CH:21]=[C:20]([Cl:23])[CH:19]=[CH:18][C:17]=1[O:16][C:15]1[C:10]2=[CH:11][C:12]([C:24]2[CH:25]=[N:26][CH:27]=[N:28][CH:29]=2)=[CH:13][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([C:24]4[CH:25]=[N:26][CH:27]=[N:28][CH:29]=4)=[CH:13][CH:14]=3)[C:9]3([CH2:8][S:7][C:6]([NH2:5])=[N:30]3)[C:22]=2[CH:21]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67250960HCID 67250960, compound

Product 1

HCID 58466273HCID 58466273, compound

Procedure

A vial was charged with rac-N-tert-butyl-2′-chloro-7′-(5-pyrimidinyl)spiro[1,3-thiazole-4,9′-xanthen]-2-amine (63.0 mg, 144 μmol) and TFA (1111 μl, 14418 μmol) resulting in a dark orange mixture. The vial was capped and placed in a 150° C. oil bath for 2 d. The reaction mixture cooled to RT, poured into 6N NaOH (aq.), and extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on a 12-g Redi-Sep column, eluting with 0-50% of a 90:10:1 mix of DCM/MeOH/NH4OH in DCM to give racemic-2′-chloro-7′-(5-pyrimidinyl)spiro[1,3-thiazole-4,9′-xanthen]-2-amine as an off-white solid. MS m/z=381.0 [M+H]+. Calc'd for C19H14ClN4OS: 381.1.

Workup

  1. customresulting in a dark orange mixture
  2. customThe vial was capped
  3. customplaced in a 150° C.
  4. customfor 2 d
  5. extractionextracted with DCM (3×)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on a 12-g Redi-Sep column
  10. washeluting with 0-50% of a 90:10:1
  11. additionmix of DCM/MeOH/NH4OH in DCM

Sources & evidence

ORD record
ord-dfb692843a304ff4a12cd85db0765e0e
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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