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p-Toluenesulfonic acid → HCID 59442735, compound

HRID 388241
Notes
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Reaction equation

HRID 388241 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[C:5]([F:19])=[CH:4][N:3]=1.[CH:20]1([C:23]2[CH:24]=[C:25]([NH2:34])[CH:26]=[C:27]([N:29]3[CH:33]=[N:32][N:31]=[N:30]3)[CH:28]=2)[CH2:22][CH2:21]1.S(O)(C1C=CC(C)=CC=1)(=O)=O>C(O)(C)C>[CH:20]1([C:23]2[CH:24]=[C:25]([NH:34][C:2]3[N:7]=[C:6]([NH:8][CH:9]4[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]4)[C:5]([F:19])=[CH:4][N:3]=3)[CH:26]=[C:27]([N:29]3[CH:33]=[N:32][N:31]=[N:30]3)[CH:28]=2)[CH2:22][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 59442725HCID 59442725, compound2×HCID 59442743HCID 59442743, compound

Product 1

HCID 59442735HCID 59442735, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 mL round bottom flask to a solution of 2-chloro-5-fluoro-N-(2,2,6,6,-tetramethylpiperidin-4-yl)pyrimidin-4-amine (Compound 11; 0.16 g, 0.56 mmol) in 10 mL isopropanol, 3-cyclopropyl-5-(1H-tetrazol-1-yl)benzenamine (0.125 g, 0.622 mmol) and TosOH (0.085 g, 0.448 mmol) were added. The reaction mixture was heated at 100° C. for 3 hours. LCMS analysis indicated the complete consumption of the mono-SNAr product and appearance of Compound III-116. The reaction mixture was then cooled to room temperature and volatiles were removed under reduced pressure. The crude reaction mixture was purified by column chromatography using DCM/2 M NH3 in MeOH to obtain Compound III-116 as a tan solid that was further purified by trituration using DCM/hexanes.

Workup

  1. customthe complete consumption of the mono-SNAr product and appearance of Compound III-116
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customvolatiles were removed under reduced pressure
  4. customThe crude reaction mixture
  5. customwas purified by column chromatography
  6. customto obtain Compound III-116 as a tan solid
  7. customthat was further purified by trituration

Sources & evidence

ORD record
ord-cd72c06954d144858119285c462a1a34
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377924B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes