Trifluoroacetic acid → HCID 178472325, compound

HRID 1499272Notes

Reaction equation

HRID 1499272 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:29][CH2:28][C:11]3([CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:46]=[C:45]4[C:41]([C:42]([CH3:47])=[N:43][NH:44]4)=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)[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[CH2:29][CH2:28][C:11]3([CH2:15][NH:14][C@H:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:46]=[C:45]4[C:41]([C:42]([CH3:47])=[N:43][NH:44]4)=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178472326HCID 178472326, compound

Product 1

HCID 178472325HCID 178472325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butyl 3-ethyl 8-(2-amino-6-((4-(3-methyl-1H-indazol-6-yl)phenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (150 mg, 0.19 mmol) in CH2Cl2 (5 mL) was added TFA (3 mL), and the resulting mixture was stirred at RT for 1 h. The reaction mixture was concentrated in vacuo, and the resulting material partitioned between CH2Cl2 and saturated NaHCO3, and extracted. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by prep-TLC (CH2Cl2/MeOH) provided (S)-ethyl 8-(2-amino-6-((4-(3-methyl-1H-indazol-6-yl)phenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate as a brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting material partitioned between CH2Cl2 and saturated NaHCO3
  3. extractionextracted
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by prep-TLC (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-b6414ea17f984bf880de226aabed0cba
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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