Acetamide → HCID 24905232, compound

HRID 238026Notes

Reaction equation

HRID 238026 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:20]4[C:15](=[N:16][CH:17]=[N:18][C:19]=4[NH2:21])[N:14]([CH:22]([CH3:24])[CH3:23])[N:13]=3)[CH:8]=2)[N:3]=1.C([NH2:28])(=O)C.C([O-])([O-])=O.[K+].[K+]>>[NH2:21][C:19]1[N:18]=[CH:17][N:16]=[C:15]2[N:14]([CH:22]([CH3:23])[CH3:24])[N:13]=[C:12]([C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[N:3]=[C:2]([NH2:28])[CH:11]=[CH:10]4)[C:20]=12

Participants

4

Reactant 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 24905216HCID 24905216, compound

Product 1

HCID 24905232HCID 24905232, compoundYield 46%

Conditions

Temperature
200 °C

Procedure

3-(2-chloroquinolin-6-yl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA130, 50 mg, 0.15 mmol), acetamide (174 mg, 3.0 mmol) and K2CO3 (104 mg, 0.75 mmol) were combined and heated to 200° C. under an argon atmosphere for one hour. Reaction was cooled, then extracted with H2O and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA146 (22 mg, 46% yield). ESI-MS (M+H)+ m/z calcd 320.2, found 320.4.

Workup

  1. customReaction
  2. temperaturewas cooled
  3. extractionextracted with H2O and CH2Cl2
  4. concentrationconcentrated in vacuo
  5. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-d49a7a876e1a48ccb9506516929f037f
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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