O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 2-(4-(4-Fluoro-3-methyl-phenyl)-2-phenyl-imidazol-1-yl)-1-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-ethanone

HRID 2402734Notes

Reaction equation

HRID 2402734 reaction equation
Cl.[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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:23]([CH2:25][C:26](O)=[O:27])[CH:24]=2)=[CH:16][C:15]=1[CH3:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:23]([CH2:25][C:26]([N:9]3[CH2:10][CH2:11][C:5]4[S:4][C:3]([CH3:2])=[N:12][C:6]=4[CH2:7][CH2:8]3)=[O:27])[CH:24]=2)=[CH:16][C:15]=1[CH3:35]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226207492-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrochlorideHCID 86686613(4-(4-Fluoro-3-methyl-phenyl)-2-phenyl-imidazol-1-yl)-acetic acid

Product 1

HCID 716572292-(4-(4-Fluoro-3-methyl-phenyl)-2-phenyl-imidazol-1-yl)-1-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-ethanoneYield 22.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

45 mg 2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrochloride was added to 60 mg (4-(4-fluoro-3-methyl-phenyl)-2-phenyl-imidazol-1-yl)-acetic acid, 70 mg TBTU, 0.06 mL TEA in 1 mL DMF. The reaction was stirred over night at RT. The mixture was purified by HPLC (ZORBAX StableBond C18; 5 μm; 30×100 mm; gradient: water (+0.3% formic acid)/acetonitril=90/10-10/90 in 9 min; flow: 50 ml/min.) to give 20 mg desired product. Rt: 0.94 (method A), (M+H)+: 461

Workup

  1. customThe mixture was purified by HPLC (ZORBAX StableBond C18; 5 μm; 30×100 mm; gradient: water (+0.3% formic acid)/acetonitril=90/10-10/90 in 9 min; flow: 50 ml/min.)

Sources & evidence

ORD record
ord-9cfff796a8684fa1964f515fdec45a3e
Source dataset
uspto-grants-2014_08
Patent number
US08796467B2

Reaction notes

Loading…