Cyclohexylamine → HCID 58382222, compound

HRID 1628018Notes

Reaction equation

HRID 1628018 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([Si](C(C)C)(C(C)C)C(C)C)[CH:14]=[CH:15][C:3]=12.[CH:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH2:11]([O:10][C:8]([C:7]1[C:2]([NH:32][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:3]2[CH:15]=[CH:14][NH:13][C:4]2=[N:5][CH:6]=1)=[O:9])[CH3:12]

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 58382073HCID 58382073, compound

Product 1

HCID 58382222HCID 58382222, compoundYield 48.2%

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.5 g, 3.9 mmol) and cyclohexylamine (2.34 g, 23.6 mmol) was stirred at about 80° C. for about 24 h. The solvent was removed under reduced pressure. The residue was suspended in Et2O and the precipitate was collected by filtration and dried under vacuum. The solid was washed with water and dried under vacuum again to give ethyl-4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.54 g, 48%): LC/MS (Table 2, Method b) Rt=2.56 min.; MS m/z: 288 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe precipitate was collected by filtration
  3. customdried under vacuum
  4. washThe solid was washed with water
  5. customdried under vacuum again

Sources & evidence

ORD record
ord-e29aa407bd574a2fa11ef5049ccafbc9
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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