Trifluoroacetic acid → HCID 131734252, compound

HRID 1499227Notes

Reaction equation

HRID 1499227 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][C:8]=2[C@@H:19]([O:24][C:25]2[N:30]=[C:29]([NH2:31])[N:28]=[C:27]([N:32]3[CH2:53][CH2:52][C:35]4([CH2:39][N:38](C(OC(C)(C)C)=O)[C@H:37]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:36]4)[CH2:34][CH2:33]3)[CH:26]=2)[C:20]([F:23])([F:22])[F:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][C:8]=2[C@@H:19]([O:24][C:25]2[N:30]=[C:29]([NH2:31])[N:28]=[C:27]([N:32]3[CH2:53][CH2:52][C:35]4([CH2:39][NH:38][C@H:37]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:36]4)[CH2:34][CH2:33]3)[CH:26]=2)[C:20]([F:22])([F:23])[F:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117952693HCID 117952693, compound

Product 1

HCID 131734252HCID 131734252, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butyl 3-ethyl 8-(6-((R)-1-([1,1′:4′,1″-terphenyl]-2′-yl)-2,2,2-trifluoroethoxy)-2-aminopyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (550 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added TFA (2.0 mL) dropwise at 0° C. The reaction mixture was stirred at RT for 2 h, and concentrated in vacuo. The pH was adjusted to 7-8 with a saturated aqueous NaHCO3 solution. The aqueous layer was extracted with CH2Cl2. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase silica gel column (CH2Cl2/MeOH) provided (S)-ethyl 8-(6-((R)-1-([1,1′:4′,1″-terphenyl]-2′-yl)-2,2,2-trifluoroethoxy)-2-aminopyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by normal phase silica gel column (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-68601edff5db4b34b3762c4bfb428aeb
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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