Trifluoroacetic acid → (S)-2-(Dimethylamino)ethyl 8-(2-amino-6-((R)-1-(4-chlor-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate

HRID 1499285Notes

Reaction equation

HRID 1499285 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:32][CH2:31][C:11]3([CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]([O:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:33][C@H:34]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=2[N:46]2[CH:50]=[CH:49][C:48]([CH3:51])=[N:47]2)[C:35]([F:38])([F:37])[F:36])[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:32][CH2:31][C:11]3([CH2:15][NH:14][C@H:13]([C:23]([O:25][CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:33][C@H:34]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=2[N:46]2[CH:50]=[CH:49][C:48]([CH3:51])=[N:47]2)[C:35]([F:36])([F:38])[F:37])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117942177HCID 117942177, compound

Product 1

HCID 117952329(S)-2-(Dimethylamino)ethyl 8-(2-amino-6-((R)-1-(4-chlor-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butyl 3-(2-(dimethylamino)ethyl) 8-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (1.4 g, 1.86 mmol) in CH2Cl2 (9 mL) was added TFA (4.5 mL), and the reaction was stirred at RT for 2 h. Then the reaction was concentrated in vacuo and the residue was partitioned between CH2Cl2 and aqueous NaHCO3, and extracted. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification via prep-HPLC column chromatography (CH2Cl2/EtOH/NH4OH) provided the title compound as an off-white solid.

Workup

  1. concentrationThen the reaction was concentrated in vacuo
  2. customthe residue was partitioned between CH2Cl2 and aqueous NaHCO3
  3. extractionextracted
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification via prep-HPLC column chromatography (CH2Cl2/EtOH/NH4OH)

Sources & evidence

ORD record
ord-83a8a6940c534504bc77594438991f20
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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