Triethylamine → HCID 50913955, compound

HRID 1949072Notes

Reaction equation

HRID 1949072 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([OH:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.CCN(CC)CC>C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2([OH:19])[CH2:18][CH2:17][N:16]([CH2:25][C:24]3[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=3)[CH2:15][CH2:14]2)=[O:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 680214-Fluorobenzyl bromideHCID 58129390HCID 58129390, compound

Product 1

HCID 50913955HCID 50913955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25.6 mg (0.09 mmol) 4-Hydroxy-piperidine-4-carboxylic acid (4-isopropyl-phenyl)-amide, 19.9 mg (0.1 mmol) 4-fluorobenzyl bromide and 27 mg (0.27 mmol) NEt3 in 2 ml DCM was stirred for 3 h at room temperature. The mixture was concentrated and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 5.4 mg (17%) of the title compound as off-white solid. MS (m/e): 371.3 [(M+H)+].

Workup

  1. concentrationThe mixture was concentrated
  2. customsubjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 5.4 mg (17%) of the title compound as off-white solid

Sources & evidence

ORD record
ord-baea424038c647ca9477a33f7d44b686
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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