Diisopropylethylamine → HCID 57377257, compound

HRID 1258897Notes

Reaction equation

HRID 1258897 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:27])[C:12]=1[C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=2)[CH:17]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:59][CH:60]1[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:27])[C:12]=1[C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH:59][CH:60]3[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)=[O:24])=[CH:20][N:19]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57378905HCID 57378905, compound

Product 1

HCID 57377257HCID 57377257, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(4-(4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinic acid (75 mg, 0.194 mmol) and TBTU (73 mg, 0.226 mmol) in DMF (2.0 mL) was added DIPEA (180 μL, 1.03 mmol). Then 4-aminotetrahydropyran (24 μL, 0.226 mmol) was added and the mixture was stirred at room temperature under Ar for 30 min. The mixture was then evaporated and purification by chromatography (reverse phase HPLC) afforded the title compound (71 mg, 77%) as a white solid. MS: m/e=448.2 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (reverse phase HPLC)

Sources & evidence

ORD record
ord-3726f4eeed104473b6d4594da03e42dd
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

Loading…