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

HRID 919577Notes

Reaction equation

HRID 919577 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]([C:26]3[C:27]4[CH:34]=[CH:33][N:32](S(C5C=CC(C)=CC=5)(=O)=O)[C:28]=4[N:29]=[CH:30][N:31]=3)[CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:8][C:6]1[CH:5]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([N:19]([C:26]3[C:27]4[CH:34]=[CH:33][NH:32][C:28]=4[N:29]=[CH:30][N:31]=3)[CH2:20][C:21]([N:23]([CH3:24])[CH3:25])=[O:22])[CH2:14]2)=[O:12])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86706453(R)-2-((1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-yl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl) amino)-N,N-dimethylacetamide

Product 1

HCID 86706455(R)-2-((1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-N,N-dimethylacetamideYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-2-((1-(2-(3,5-dichlorophenylamino) acetyl) piperidin-3-yl) (7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-N, N-dimethylacetamide (45 mg, 0.068 mmol) and K2CO3 (37 mg, 0.27 mmol) in MeOH (5 mL) was heated at 70° C. for 2 h. The solvent was then evaporated in vacuo to give a solid, which was purified by column chromatography (silica gel, gradient 0-3% methanol in chloroform) to afford the titled compound (14 mg, 41%). 1H NMR (400 MHz, CDCl3): δ 10.19 (s, 1H), 8.32 and 8.23 (2s, 1H), 7.04 (s, 1H), 6.66 (s, 1H), 6.48 (s, 1H), 6.18 (s, 1H), 5.21 (s, 1H), 4.65-4.64 (m, 2H), 4.41-4.20 (m, 3H), 3.80-3.76 (m, 1H), 3.20 (s, 3H), 3.05 (s, 3H), 3.02-2.88 (m, 2H), 2.60 (t, J=11.6 Hz, 1H), 2.36 (t, J=11.6 Hz, 1H), 1.99-1.67 (m, 4H). LCMS [M+1]: 504, [M+23]: 526.

Workup

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

Sources & evidence

ORD record
ord-8110e70768fd44fcbf8622f0830a2e79
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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