Water → HCID 68778456, compound

HRID 2263008Notes

Reaction equation

HRID 2263008 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[N:3]=1.FC(F)(F)C(O)=O.[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([NH:30][C:31]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[O:32])=[N:22]1.C(N(CC)CC)C.O>CN(C)C=O>[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([NH:30][C:31]([N:33]2[CH2:38][CH2:37][N:36]([C:2]3[S:6][N:5]=[C:4]([N:7]4[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]4)[N:3]=3)[CH2:35][CH2:34]2)=[O:32])=[N:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetateHCID 68778582HCID 68778582, compound

Product 1

HCID 68778456HCID 68778456, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-chloro-1,2,4-thiadiazol-3-yl)piperidin-4-ol (153 mg, 0.555 mmol) and N-1,2-benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate (200 mg, 0.555 mmol) in N,N-dimethylformamide (2 ml) was added triethylamine (0.387 ml, 2.78 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured to water, and a solid was separated by filtration and washed with water, which was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to give 79.0 mg (33.2%) of the desired product as a solid.

Workup

  1. customa solid was separated by filtration
  2. washwashed with water, which
  3. customwas recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-0ca600ffad884f3186ba9388098cf18d
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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