Diisopropylethylamine → 1-(4-Benzo[d]isoxazol-3-yl-piperidin-1-yl)-2-(3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-ethanone

HRID 239192Notes

Reaction equation

HRID 239192 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH:56]1[CH2:61][CH2:60][CH:59]([C:62]2[C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][C:65]=3[O:64][N:63]=2)[CH2:58][CH2:57]1>CN(C=O)C>[O:64]1[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=2[C:62]([CH:59]2[CH2:60][CH2:61][N:56]([C:21](=[O:22])[CH2:20][N:10]3[C:11]([C:13]4[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=4)=[N:12][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9]3)[CH2:57][CH2:58]2)=[N:63]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 130764373-(4-Piperidinyl)-1,2-benzisoxazole HydrochlorideHCID 86686517(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid

Product 1

HCID 715865941-(4-Benzo[d]isoxazol-3-yl-piperidin-1-yl)-2-(3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-ethanoneYield 39.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 mg (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid was dissolved in 2 mL DMF. 32 mg TBTU and 26 μL DIPEA were added to this solution and the mixture was stirred for 5 minutes at RT. Then, 24 mg 3-piperidin-4-yl-benzo[d]isoxazolehydrochloride was added. The mixture was stirred for 2 h at RT. The reaction solution was purified by HPLC to yield 19.8 mg of the desired compound. Rt: 2.24 (method D), (M+H)+: 500

Workup

  1. stirringThe mixture was stirred for 2 h at RT
  2. customThe reaction solution was purified by HPLC

Sources & evidence

ORD record
ord-82730492f79d44858652b9a1fa0e58b2
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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