Triethylamine → HCID 68165073, compound

HRID 921283Notes

Reaction equation

HRID 921283 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([P:19]([CH3:22])([CH3:21])=[O:20])=[CH:15][CH:14]=2)[N:3]=1.C([N:25]([CH2:28][CH3:29])CC)C.Cl.N[C@H:32]1CC[O:34][CH2:33]1>C(O)C>[CH3:21][P:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:25][CH:28]3[CH2:29][CH2:32][CH2:33][O:34]3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)([CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 86668788HCID 86668788, compound

Product 1

HCID 68165073HCID 68165073, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine (prepared as in Example 1: 40 mg, 0.12 mmol) in 2 mL of ethanol was added 50 L of triethylamine and (s)-3-aminotetrahydrofuran hydrochloride salt (14 mg, 0.12 mmol). The mixture was microwave at 120 degrees for 20 minutes. The reaction mixture was filtered through a syringe filter and purified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield a white solid as product (27 mg, 59% yield.) MS/ES+: m/z=401.

Workup

  1. customat 120 degrees
  2. customfor 20 minutes
  3. filtrationThe reaction mixture was filtered through a syringe
  4. filtrationfilter
  5. custompurified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases)
  6. customto yield a white solid as product (27 mg, 59% yield.) MS/ES+

Sources & evidence

ORD record
ord-ca553bbd96404067b5b867ea21764fb9
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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