Tetrahydrofuran → HCID 68692401, compound

HRID 1445481Notes

Reaction equation

HRID 1445481 reaction equation
C1C[O:4][CH2:3]C1.[H-].[Na+].[NH2:8][C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12].[C:21]([C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C@@H:34]([CH3:35])[CH2:33][N:32]([C:36](Cl)=[O:37])[C@H:31]([CH3:39])[CH2:30]2)=[CH:25][C:24]=1C(F)(F)F)#[N:22]>O>[C:11]([C:10]1[CH:13]=[CH:14][C:15]([C:17]([F:18])([F:19])[F:20])=[CH:16][C:9]=1[NH:8][C:36]([N:32]1[CH2:33][C@H:34]([CH3:35])[N:29]([C:26]2[CH:27]=[CH:28][C:23]([C:21]#[N:22])=[C:24]([O:4][CH3:3])[CH:25]=2)[CH2:30][C@H:31]1[CH3:39])=[O:37])#[N:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 134390282-Amino-4-(trifluoromethyl)benzonitrileHCID 86601759HCID 86601759, compound

Product 1

HCID 68692401HCID 68692401, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 10 ml of THF was suspended 80 mg of 60% NaH, and then 337 mg of 2-amino-4-trifluoromethylbenzonitrile was added thereto at room temperature, followed by 30 minutes of stirring at room temperature. Then, 558 mg of (2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethylpiperazine-1-carbonyl chloride was added thereto, followed by 17 hours of stirring at room temperature. Water was added to the reaction solution, followed by extraction with chloroform. After the organic layer was washed with water, the solvent was removed by evaporation. The resulting residue was subjected to silica gel column chromatography to obtain 358 mg of the title compound from an eluate using hexane-ethyl acetate (1:1, v/v).

Workup

  1. waitfollowed by 17 hours
  2. stirringof stirring at room temperature
  3. extractionfollowed by extraction with chloroform
  4. washAfter the organic layer was washed with water
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-60c4e99e35ea4f739f03ee0e2c0281d8
Source dataset
uspto-grants-2010_02
Patent number
US07666873B2

Reaction notes

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