Trifluoroacetic acid → (S)-3-(2-(((S)-1-(4-((3,3-dimethylpiperazin-1-yl)methyl)phenyl)ethyl)amino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one

HRID 1850207Notes

Reaction equation

HRID 1850207 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([C:19]2[CH:40]=[CH:39][C:22]([CH2:23][N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[C:26]([CH3:38])([CH3:37])[CH2:25]3)=[CH:21][CH:20]=2)[CH3:18])[N:11]=1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(Cl)Cl>[CH3:38][C:26]1([CH3:37])[NH:27][CH2:28][CH2:29][N:24]([CH2:23][C:22]2[CH:39]=[CH:40][C:19]([C@@H:17]([NH:16][C:12]3[N:11]=[C:10]([N:5]4[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])[CH:15]=[CH:14][N:13]=3)[CH3:18])=[CH:20][CH:21]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 86730161tert-butyl 4-(4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzyl)-2,2-dimethylpiperazine-1-carboxylate

Product 1

HCID 86730257(S)-3-(2-(((S)-1-(4-((3,3-dimethylpiperazin-1-yl)methyl)phenyl)ethyl)amino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-oneYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzyl)-2,2-dimethylpiperazine-1-carboxylate (78 mg, 0.14 mmol) in DCM (1 mL) was added TFA (1 mL, 12 mmol) slowly at −78° C. The reaction was stirred at room temperature for 1 h then was concentrated and diluted with DCM (10 mL). The solution was stirred with 3 eq. of MP-carbonate resin (3.28 mmol/g, Biotage) for 1 h at room temperature. The resin was removed by filtration and washed (2×5 mL) with DCM. The filtrate was concentrated and purified through HPLC to give (S)-3-(2-(((S)-1-(4-((3,3-dimethylpiperazin-1-yl)methyl)phenyl)ethyl)amino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one as a white solid (23 mg, 36% yield).

Workup

  1. concentrationthen was concentrated
  2. additiondiluted with DCM (10 mL)
  3. customThe resin was removed by filtration
  4. washwashed (2×5 mL) with DCM
  5. concentrationThe filtrate was concentrated
  6. custompurified through HPLC

Sources & evidence

ORD record
ord-b1357073f20542089957cb4399143db9
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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