Water → HCID 86275528, compound

HRID 2202108Notes

Reaction equation

HRID 2202108 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][N:15]([CH3:26])[CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)=[CH:12][N:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].O.CC#N>ClCCl.FC(F)(F)C(O)=O>[NH2:18][CH2:17][CH2:16][N:15]([CH2:14][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[N:10]=[N:11][CH:12]=1)[CH3:26]

Participants

6

Reactant 3

HCID 962WaterHCID 6342Acetonitrile2×HCID 90463647HCID 90463647, compound

Product 1

HCID 86275528HCID 86275528, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl N-[2-([[1-(4-cyanophenyl)-1H-1,2,3-triazol-5-yl]methyl](methyl)amino)ethyl]carbamate (100 mg, 0.28 mmol, 1.00 equiv) in dichloromethane (4 mL) and trifluoroacetic acid (4 mL) was stirred at room temperature for 2 h. The resulting mixture was concentrated under vacuum and the crude product was purified by Prep-HPLC with the following conditions (2#-Waters 2767-2(HPLC-08)): Column, XBridge Shield RP 18, 5 μm, 19*×150 mm; mobile phase, water with 50 mmol NH4HCO3 and CH3CN (10.0% CH3CN up to 28.0% in 2 min, up to 46.0% in 10 min, up to 100.0% in 1 min, down to 10.0% in 1 min); Detector, UV 254 nm to give 41.6 mg (58%) of 4-(5-(((2-aminoethyl)(methyl)amino)methyl)-1H-1,2,3-triazol-1-yl)benzonitrile as a white solid. 1H NMR (400 MHz, CD3OD) δ: 8.04-7.91 (s, 5H), 3.76 (s, 2H), 2.76 (t, J˜6.2 Hz, 2H), 2.53 (t, J˜6.2 Hz, 2H), 2.21 (s, 3H) ppm. LCMS (method H, ESI): RT=1.02 min, m/z=257.1 [M+H]+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customthe crude product was purified by Prep-HPLC with the following conditions (2#-Waters 2767-2(HPLC-08))
  3. waitup to 100.0% in 1 min
  4. waitdown to 10.0% in 1 min)

Sources & evidence

ORD record
ord-a6edfe3ff780410bb0512f0f6bfd0f58
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

Loading…