Triethylamine → HCID 135511675, compound

HRID 491145Notes

Reaction equation

HRID 491145 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C@@H:16]([C:27]([OH:29])=O)[CH2:17][C:18]3[CH:23]=[C:22]([CH3:24])[C:21]([OH:25])=[C:20]([CH3:26])[CH:19]=3)=[O:14])[CH2:9][CH2:8]2)[N:5]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[O:65]1[CH2:70][CH2:69][CH:68]([N:71]2[CH2:76][CH2:75][NH:74][CH2:73][CH2:72]2)[CH2:67][CH2:66]1>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C@H:16]([CH2:17][C:18]3[CH:19]=[C:20]([CH3:26])[C:21]([OH:25])=[C:22]([CH3:24])[CH:23]=3)[C:27](=[O:29])[N:74]3[CH2:73][CH2:72][N:71]([CH:68]4[CH2:69][CH2:70][O:65][CH2:66][CH2:67]4)[CH2:76][CH2:75]3)=[O:14])[CH2:11][CH2:12]2)[N:5]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 219423151-(Oxan-4-yl)piperazineHCID 136335820HCID 136335820, compound

Product 1

HCID 135511675HCID 135511675, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.21 mmol) (R)-1-carboxy-2-(4-hydroxy-3,5-dimethyl-phenyl)-ethyl 4-(5-oxo-3-phenyl-4,5-dihydro-1,2,4-triazol-1-yl)-piperidine-1-carboxylate, 74 mg (0.23 mmol) TBTU and 35 μL (0.26 mmol) triethylamine in 1 mL DMF was stirred for 1 h at RT. Then 35 mg (0.21 mmol) 1-(tetrahydropyran-4-yl)-piperazine was added and the reaction mixture was stirred for a further 5 h at RT. The reaction solution was purified by HPLC without any further working up. The fractions containing the product were combined and lyophilised.

Workup

  1. customThe reaction solution was purified by HPLC without
  2. additionThe fractions containing the product

Sources & evidence

ORD record
ord-bee2d89427e848d9814ac5773d771a1a
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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