Potassium Carbonate → HCID 58015990, compound

HRID 2189318Notes

Reaction equation

HRID 2189318 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[CH:19][C:20]4[CH:25]=[C:24]([CH:26]=[O:27])[N:23]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1(C)C=CC(S([N+:42]#[C-:43])(=O)=O)=CC=1.[C:45]([O-])([O-])=O.[K+].[K+]>CO>[CH2:31]([CH:28]([N:23]1[C:21]2[N:22]=[C:17]([NH:16][C:13]3[CH:14]=[CH:15][C:10]([N:7]4[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]4)=[CH:11][CH:12]=3)[N:18]=[CH:19][C:20]=2[CH:25]=[C:24]1[C:26]1[O:27][CH:43]=[N:42][CH:45]=1)[CH2:29][CH3:30])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11788634HCID 11788634, compoundHCID 23624284HCID 23624284, compound

Product 1

HCID 58015990HCID 58015990, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (30 mg, 0.07 mmol) in MeOH (1 mL) are added p-toluenesulfonyl isocyanide (16 mg, 0.08 mmol) and K2CO3 (29 mg, 0.21 mmol). The reaction mixture is heated at reflux for 1.5 h and concentrated in vacuo. The residue is purified by preparative HPLC to give 21 mg of 1-(4-{4-[7-(1-ethyl-propyl)-6-oxazol-5-yl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone as a pale brown solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 1.5 h
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-86d77a8b69774e93980504c175a0c418
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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