Triethylamine → HCID 24829220, compound

HRID 2405992Notes

Reaction equation

HRID 2405992 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH2:15])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[C:17]1[C:18]2[CH:25]=[CH:24][NH:23][C:19]=2[N:20]=[CH:21][N:22]=1.C(N(CC)CC)C>C(O)CCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH2:15])[CH2:10][CH2:11][N:12]([C:17]3[C:18]4[CH:25]=[CH:24][NH:23][C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 66888877HCID 66888877, compound

Product 1

HCID 24829220HCID 24829220, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-(4-chlorophenyl)piperidin-4-yl amine hydrochloride (0.030 g, 0.1058 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.016 g, 0.1058 mmol) and triethylamine (0.074 ml, 0.5289 mmol) in n-butanol (1.0 ml) was heated to 100° C. for 2 days. Concentration and purification by SCX-2 Isolute column (2 g), eluting with 1M NH3/MeOH, followed by silica column chromatography (20% methanol in DCM) gave a white solid (0.026 g, 74%). LC-MS (LCT2) m/z 328 [M+H+], Rt 2.59 min.

Workup

  1. concentrationConcentration and purification by SCX-2 Isolute column (2 g)
  2. washeluting with 1M NH3/MeOH

Sources & evidence

ORD record
ord-b22a55ba131a4fc6b911349ecc11c01c
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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