Diisopropylethylamine → 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

HRID 550845Notes

Reaction equation

HRID 550845 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][CH2:10][CH:11]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.C(N(C(C)C)CC)(C)C.C1([O:43][C:44](=O)[NH:45][C:46]2[S:47][C:48]3[N:49]=[CH:50][N:51]=[C:52]([O:55][CH3:56])[C:53]=3[N:54]=2)C=CC=CC=1>C(#N)C>[CH3:56][O:55][C:52]1[C:53]2[N:54]=[C:46]([NH:45][C:44]([N:25]3[CH2:26][CH2:27][N:22]([CH:11]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=4)[CH2:10][O:9][CH3:8])[CH2:23][CH2:24]3)=[O:43])[S:47][C:48]=2[N:49]=[CH:50][N:51]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59011944(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl esterHCID 866165091-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine trifluoroacetate

Product 1

HCID 248306114-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amideYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine trifluoroacetate (160 mg, 0.40 mmol) and diisopropylethylamine (0.35 mL, 2.0 mmole) in acetonitrile (10 mL) was heated at 70° C. for ten minutes. After cooling to room temperature, (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester (120 mg, 0.40 mmol) was added to the above solution. The mixture was stirred at reflux for three hours. LCMS analysis indicated complete consumption of starting material. The reaction was concentrated and the crude was purified using reversed phase HPLC to give 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (81 mg, 41% yield) as a white powder. LRMS for C21H23F3N6O3S (M+H)+ at m/z=497. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureat reflux for three hours
  3. customconsumption of starting material
  4. concentrationThe reaction was concentrated
  5. customthe crude was purified

Sources & evidence

ORD record
ord-bf4f7b464e46492482aac50877825e9d
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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