1-Chloroethyl chloroformate → 4,5,6,7-Tetrahydro-1-(2-pyridinyl)-1H-imidazo[4,5-c]pyridine

HRID 2177560Notes

Reaction equation

HRID 2177560 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=[N:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[N:16]=[CH:15]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 904091645-Benzyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

Product 1

HCID 904084924,5,6,7-Tetrahydro-1-(2-pyridinyl)-1H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-benzyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine (0.13 g, 0.45 mmol) in DCE (5 mL) was added 1-chloroethyl chloroformate (0.10 mL, 0.90 mmoL). The reaction was allowed to stir for 15 min then heated at reflux for 4 h. The reaction was let cool, concentrated, dissolved in MeOH and heated again at 60° C. for 1 h. The reaction was concentrated and the product was used in the next step without further purification (0.075 g, 83%). MS (ESI): mass calculated for C11H12N4, 200.1. m/z found 201.2 [M+H]+.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction was let cool
  4. concentrationconcentrated
  5. dissolutiondissolved in MeOH
  6. concentrationThe reaction was concentrated
  7. customthe product was used in the next step without further purification (0.075 g, 83%)

Sources & evidence

ORD record
ord-9729992591a94276a8d2fcc080818b3d
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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