HCID 24905296, compound → HCID 24905197, compound

HRID 238024Notes

Reaction equation

HRID 238024 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][CH:12]=[N:13][C:14]([NH2:15])=[C:9]3[C:8]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([O:25]C)[CH:17]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl>[NH2:15][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([OH:25])[CH:17]=3)[C:9]=12

Participants

3

Reactant 1

HCID 24905296HCID 24905296, compound

Product 1

HCID 24905197HCID 24905197, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

1-cyclopentyl-3-(4-ethoxy-3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (ZK359, 25 mg, 0.071 mmol) was dissolved in CH2Cl2 (5 ml) and stirred at −10° C. under an argon atmosphere. After 30 minutes, reaction was brought to 0° C. and stirred for 2.5 hours. Reaction was stirred for additional 4 hours at room temperature, then concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA98 (3 mg, 13% yield). ESI-MS (M+H)+ m/z calcd 340.1, found 340.1.

Workup

  1. customreaction
  2. customwas brought to 0° C.
  3. stirringstirred for 2.5 hours
  4. customReaction
  5. stirringwas stirred for additional 4 hours at room temperature
  6. concentrationconcentrated in vacuo
  7. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-c2860a91fce1489aafba6245fa75bdb4
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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