Hydrazine hydrate (1:1) → HCID 24905239, compound

HRID 238027Notes

Reaction equation

HRID 238027 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([CH3:22])[CH3:21])[N:9]=[C:10]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13](F)[CH:12]=3)[C:3]=12.O.[NH2:24][NH2:25]>CCCCO>[NH2:16][C:15]1[C:14]2[C:13](=[CH:12][C:11]([C:10]3[C:3]4[C:4](=[N:5][CH:6]=[N:7][C:2]=4[NH2:1])[N:8]([CH:20]([CH3:22])[CH3:21])[N:9]=3)=[CH:18][CH:17]=2)[NH:25][N:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 24905237HCID 24905237, compound

Product 1

HCID 24905239HCID 24905239, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorobenzonitrile (BA150, 20 mg, 0.07 mmol) was dissolved in n-BuOH (2 ml). Hydrazine monohydrate (0.400 ml) was added and the reaction was heated to 110° C. under an argon atomosphere and left stirring over night. Reaction mixture was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA154 (15 mg, 70% yield). ESI-MS (M+H)+ m/z calcd 309.2, found 309.4.

Workup

  1. waitleft
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-14bdfdcf106d496aad399c5e135ec550
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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