Potassium Carbonate → (R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone

HRID 919575Notes

Reaction equation

HRID 919575 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([N:19]([CH2:39][CH2:40][OH:41])[C:20]3[C:21]4[CH:28]=[CH:27][N:26](S(C5C=CC(C)=CC=5)(=O)=O)[C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([N:19]([CH2:39][CH2:40][OH:41])[C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69676522(R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone

Product 1

HCID 56969657(R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanoneYield 46.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone (400 mg, 0.649 mmol) and K2CO3 (341 mg, 2.46 mmol) in MeOH (16 mL) was heated at 70° C. for 2 h. The solvent was concentrated in vacuo to give a solid, which was purified by column chromatography (silica gel, gradient 0-4% methanol in chloroform) to afford the titled compound (0.14 g, 46%). 1H NMR (400 MHz, DMSO-d6): 11.73 and 11.68 (2s, 1H), 8.12 (d, J=6.4 Hz, 1H), 7.35 (s, 1H), 7.20 and 7.15 (2s, 1H), 6.76 (s, 1H), 6.69 and 6.56 (2s, 1H), 6.62 and 6.49 (2s, 1H), 6.37-6.34 (m, 1H), 5.10-5.00 (m, 1H), 4.69-4.60 (m, 1H), 4.49-4.39 (m, 1H), 4.14-3.88 (m, 3H), 3.79-3.59 (m, 3H), 3.18 and 2.99 (2t, J=12.4 Hz, 1H), 2.84 and 2.70 (2t, J=12.4 Hz, 1H), 2.61-2.57 (m, 1H), 2.02-1.81 (m, 3H), 1.65-1.49 (m, 1H). LCMS [M+1]: 463.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customto give a solid, which
  3. customwas purified by column chromatography (silica gel, gradient 0-4% methanol in chloroform)

Sources & evidence

ORD record
ord-0e8960fce8014083be2559e9f685f094
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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