Trifluoroacetic acid → HCID 178441807, compound

HRID 705137Notes

Reaction equation

HRID 705137 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([NH:26]CC2C=CC(OC)=C(OC)C=2)[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>>[CH2:1]([C:5]1[N:6]=[C:7]([NH2:26])[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178441822HCID 178441822, compound

Product 1

HCID 178441807HCID 178441807, compoundYield 39.2%

Procedure

A solution of (S)-5-butyl-N-(3,4-dimethoxybenzyl)-3-(6-(3-fluoropyrrolidin-1-yl)hexyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (119 mg, 0.232 mmol) in trifluoroacetic acid (1 mL, 12.98 mmol) was heated in a Biotage Initiator microwave (using initial absortion setting high) at 120° C. for 2.5 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in 3:1 chloroform:IPA (50 mL) and washed with aqueous sodium hydroxide (0.1 M, 50 mL). The organic phase was separated and the aqueous back extracted with 3:1 chloroform:IPA (30 mL). The combined organic extracts were dried (hydrophobic frit) and concentrated in vacuo. The material (223 mg) 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 orange solid (33 mg).

Workup

  1. customat 120° C.
  2. customfor 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 3:1 chloroform
  5. washIPA (50 mL) and washed with aqueous sodium hydroxide (0.1 M, 50 mL)
  6. customThe organic phase was separated
  7. extractionthe aqueous back extracted with 3:1 chloroform
  8. customThe combined organic extracts were dried (hydrophobic frit)
  9. concentrationconcentrated in vacuo
  10. dissolutionThe material (223 mg) was dissolved in MeOH:DMSO (1:1) (2 mL)
  11. custompurified by MDAP (Method B)
  12. customevaporated in-vacuo

Sources & evidence

ORD record
ord-67531c8491cf4b97b5d73febc645a6d2
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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