Diisopropylethylamine → 2-[1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl]-1-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-ethanone

HRID 1019641Notes

Reaction equation

HRID 1019641 reaction equation
Br.[CH3:2][C:3]1[S:4][C:5]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[N:12]=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:9]2[CH2:10][CH2:11][C:5]3[S:4][C:3]([CH3:2])=[N:12][C:6]=3[CH2:7][CH2:8]2)=[O:35])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866879412-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrobromideHCID 89620421(1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid lithium salt

Product 1

HCID 716042662-[1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl]-1-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-ethanoneYield 44.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

38 mg 2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrobromide was added to 40 mg (1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid lithium salt, 45 mg TBTU, 0.06 mL DIPEA in 0.75 mL DMF. The reaction was stirred over night at RT. Water was added to the reaction and the mixture was stirred 1 h. The precipitate was filltered and dried to give 26 mg desired product. Rt: 4.59 (method E), (M+H)+: 465

Workup

  1. stirringthe mixture was stirred 1 h
  2. customdried

Sources & evidence

ORD record
ord-30fb56a5f8984f59b4801a664d1d5098
Source dataset
uspto-grants-2014_05
Patent number
US08716277B2

Reaction notes

Loading…