Trifluoroacetic acid → HCID 178441806, compound

HRID 705136Notes

Reaction equation

HRID 705136 reaction equation
[N:1]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[C:18]3[N:19]=[C:20]([CH2:35][CH2:36][CH2:37][CH3:38])[N:21]=[C:22]([NH:23]CC4C=CC(OC)=CC=4OC)[C:17]=3[NH:16][N:15]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>>[N:1]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[C:18]3[N:19]=[C:20]([CH2:35][CH2:36][CH2:37][CH3:38])[N:21]=[C:22]([NH2:23])[C:17]=3[NH:16][N:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178441813HCID 178441813, compound

Product 1

HCID 178441806HCID 178441806, compoundYield 220.6%

Conditions

Temperature
60 °C

Procedure

3-(6-(Azepan-1-yl)hexyl)-5-butyl-N-(2,4-dimethoxybenzyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (0.100 g, 0.191 mmol) was dissolved in trifluoroacetic acid (2 mL, 26.0 mmol) at ambient temperature. The reaction mixture was stirred at 60° C. for 4 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in 3:1 chloroform:IPA (15 mL) and washed with aqueous sodium hydroxide (0.1 M, 5 mL). The organic phase was separated using a hydrophobic frit and evaporated in vacuo to give a brown oil (0.157 g). The oil was dissolved in MeOH:DMSO (1:1) (2 mL) and purified by MDAP (Method B). Appropriate fractions were combined and evaporated in-vacuo to yield the title compound as an off-white solid (38 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 3:1 chloroform
  3. washIPA (15 mL) and washed with aqueous sodium hydroxide (0.1 M, 5 mL)
  4. customThe organic phase was separated
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d736720933c1434c85dcd481bb97dbdd
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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