Triethylamine → HCID 178483820, compound

HRID 526566Notes

Reaction equation

HRID 526566 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2].CCN(CC)CC.[C:31]([O:35][C:36](=[O:43])[N:37]([CH2:39][CH2:40][CH2:41][NH2:42])[CH3:38])([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:42][CH2:41][CH2:40][CH2:39][N:37]([CH3:38])[C:36](=[O:43])[O:35][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:21])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756543tert-butyl N-(3-aminopropyl)-N-methylcarbamateHCID 178509615HCID 178509615, compound

Product 1

HCID 178483820HCID 178483820, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (200 mg, 0.65 mmol) HATU (372 mg, 0.98 mmol), and Et3N (198 mg, 1.96 mmol) in DMF (3.0 mL). The mixture was stirred at room temperature for 0.5 hour, then tert-butyl(3-aminopropyl)(methyl)carbamate (147.39 mg, 0.79 mmol) was added. The mixture was stirred overnight at room temperature. The reaction mixture was purified by preparative HPLC to give tert-butyl (3-(6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinamido)propyl)(methyl)carbamate (150 mg, 48%).

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-3668d2af6c774f038ac86b23d07a5302
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

Loading…