Trifluoroacetic acid → 2-(2-(2-(2-(4-(3-Aminooxetan-3-yl)phenylamino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 1779092Notes

Reaction equation

HRID 1779092 reaction equation
C(O)(C(F)(F)F)=O.CC(C)(S([NH:13][C:14]1([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]3[N:30]=[C:29]([CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[CH2:39][C:40]([NH2:42])=[O:41])[C:28]([CH3:43])=[CH:27][N:26]=3)=[CH:20][CH:19]=2)[CH2:17][O:16][CH2:15]1)=O)C>C(Cl)Cl>[NH2:13][C:14]1([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]3[N:30]=[C:29]([CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[CH2:39][C:40]([NH2:42])=[O:41])[C:28]([CH3:43])=[CH:27][N:26]=3)=[CH:20][CH:19]=2)[CH2:15][O:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712727HCID 86712727, compound

Product 1

HCID 730560392-(2-(2-(2-(4-(3-Aminooxetan-3-yl)phenylamino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamideYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to a solution of 2-(2-(2-(2-(4-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)phenylamino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (A122) (30 mg, 0.058 mmol) in DCM (3.0 mL) under a nitrogen atmosphere and the resulting mixture stirred at room temperature for 30 minutes, then at 35° C. overnight. The volatiles were evaporated under reduced pressure, keeping the temperature below 30° C. The resulting oil was purified by semi preparative HPLC, to give the title compound 31 (5.0 mg, 21%); 1H NMR (300 MHz, d4-MeOH) δ 8.24 (br s, 1H), 8.15 (s, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.38 (d, J=8.8 Hz, 2H), 7.22 (m, 4H), 5.13 (d, J=7.7 Hz, 2H), 4.97 (d, J=7.7 Hz, 2H), 3.67 (s, 2H), 3.16 (m, 2H), 3.00 (m, 2H), 2.13 (s, 3H). LCMS: rt 4.72 min; m/z 418.2 [M+H]+.

Workup

  1. customat 35° C.
  2. customovernight
  3. customThe volatiles were evaporated under reduced pressure
  4. customthe temperature below 30° C
  5. customThe resulting oil was purified by semi preparative HPLC

Sources & evidence

ORD record
ord-504179c73a504d8f9019b9ebbcbed0b2
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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