Diisopropylethylamine → 2-(1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-1-(4-[1,3,5]triazin-2-yl-piperazin-1-yl)-ethanone

HRID 1428950Notes

Reaction equation

HRID 1428950 reaction equation
[N:1]1[CH:6]=[N:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[Li+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:23]=[C:22]2[CH2:33][C:34]([O-])=[O:35])=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:23]=[C:22]2[CH2:33][C:34]([N:10]2[CH2:9][CH2:8][N:7]([C:2]3[N:3]=[CH:4][N:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]2)=[O:35])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27606732-(Piperazin-1-yl)-1,3,5-triazineHCID 89620421(1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid lithium salt

Product 1

HCID 715997722-(1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-1-(4-[1,3,5]triazin-2-yl-piperazin-1-yl)-ethanoneYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

22 mg 1-(1,3,5-triazin-2-yl)-piperazine was added to 40 mg (1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid lithium salt, 45 mg TBTU, 0.03 mL DIPEA in 0.75 mL DMF. The reaction was stirred overnight at RT. 5 mL water was added to the reaction and the mixture was stirred 1 h. The precipitate was filtered and dried to give 37 mg desired product.

Workup

  1. stirringthe mixture was stirred 1 h
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-0bd3b8d641e5473daa1a3b759765c740
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

Loading…