Acetic Acid → HCID 67007674, compound

HRID 1187729Notes

Reaction equation

HRID 1187729 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH:20]([C:23](O)=[O:24])[CH2:19][CH2:18]3)[CH:14]=[C:13]([NH:26][C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.[CH3:33][S:34]([NH2:37])(=[O:36])=[O:35].C1CCN2C(=NCCC2)CC1.C(O)(=O)C>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:18][CH2:19][CH:20]([C:23]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])=[O:24])[CH2:21][CH2:22]3)[CH:14]=[C:13]([NH:26][C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 56600792HCID 56600792, compound

Product 1

HCID 67007674HCID 67007674, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Under argon atmosphere, 92 mg of (S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidine-4-carboxylic acid (Example 85) was dissolved in 2 ml of tetrahydrofuran, and 41 mg of N,N′-carbonyldiimidazole was added thereto, and the mixture was stirred at 70° C. for 1 hour. The reaction solution was air-cooled to room temperature, and 80 mg of methanesulfonamide and 63 μl of 1,8-diazabicyclo[5,4,0]-7-undecene were added thereto, and the mixture was stirred at room temperature for 4 hours. The reaction solution was diluted with water, and the pH of the mixture was adjusted to 4 by using acetic acid. The reaction solution was subjected to extraction with ethyl acetate, and the organic layer was washed in turn with water and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 42 mg of the objective compound as white powder.

Workup

  1. temperatureThe reaction solution was air-cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionThe reaction solution was subjected to extraction with ethyl acetate
  4. washthe organic layer was washed in turn with water and brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0e3c481773e741e99476dabdce3c7b45
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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