Trifluoroacetic acid → 2-(2-(2-(2-((2-Methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 705739Notes

Reaction equation

HRID 705739 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9](=[O:51])[CH2:10][C:11]1[CH:50]=[CH:49][CH:48]=[CH:47][C:12]=1[CH2:13][CH2:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]=[C:17]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[CH:28][C:27]=2[O:45][CH3:46])[N:16]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:46][O:45][C:27]1[CH:28]=[C:29]([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:30]=[CH:31][C:26]=1[NH:25][C:17]1[N:16]=[C:15]([CH2:14][CH2:13][C:12]2[CH:47]=[CH:48][CH:49]=[CH:50][C:11]=2[CH2:10][C:9]([NH2:8])=[O:51])[C:20]([C:21]([F:22])([F:23])[F:24])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68283338tert-Butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate

Product 1

HCID 601619862-(2-(2-(2-((2-Methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (1 mL) was added to a stirred solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate (I23) (185 mg, 0.301 mmol) in DCM (10 mL) and the resulting solution was stirred at room temperature for 2 hours. DCM (20 mL) and 10% NaHCO3 solution (10 mL) were added then the organic layer was dried (MgSO4) and evaporated to dryness under reduced pressure to give the title compound (2) (125 mg, 81%) as a colourless solid; 1H NMR (400 MHz, CD2Cl2) δ 8.49 (s, 1H), 8.31 (d, J=8.3 Hz, 1H), 7.91 (s, 1H), 7.28-7.12 (m, 3H), 6.94 (bs, 2H), 6.85 (d, J=8.2 Hz, 1H), 6.78 (dd, J=11.8, 3.1 Hz, 1H), 6.35 (s, 1H), 5.94 (s, 1H), 3.88 (s, 3H), 3.65 (s, 2H), 3.42 (d, J=12.3 Hz, 2H), 3.24-3.02 (m, 4H), 2.91 (t, J=11.3 Hz, 2H), 2.75-2.61 (m, 1H), 2.10-1.83 (m, 4H). LCMS Method C: rt 4.92 min; m/z 514.1 [M+1]+, 521.1 [M−1].

Workup

  1. dry with materialthe organic layer was dried (MgSO4)
  2. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-99361fd5d6094dbe8d7ffd03e931d858
Source dataset
uspto-grants-2015_11
Patent number
US09174946B2

Reaction notes

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