(Diethylamino)sulfur trifluoride → HCID 58008750, compound

HRID 1502498Notes

Reaction equation

HRID 1502498 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:13][C:14]3[N:15]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])[C:16](=[O:25])[C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[N:9]=[C:10]([CH2:11]O)[C:3]=12.C(N(S(F)(F)[F:39])CC)C>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:13][C:14]3[N:15]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])[C:16](=[O:25])[C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[N:9]=[C:10]([CH2:11][F:39])[C:3]=12

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58008593HCID 58008593, compound2×

Product 1

HCID 58008750HCID 58008750, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3-((4-amino-3-(hydroxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one (compound 4503) (50 mg, 0.12 mmol) in anhydrous DCM (2 mL) at 0° C. under an argon atmosphere, diethylaminosulfur trifluoride (DAST, 77 μL, 0.59 mmol) was slowly added and the resulting mixture was stirred from 0° C. to room temperature for 5 h. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by prep-TLC plate (7% MeOH/DCM) to afford the desired product, 3-((4-amino-3-(fluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one (4504, compound 310 in Table 4) (10.3 mg, 20% yield) as a white solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by prep-TLC plate (7% MeOH/DCM)

Sources & evidence

ORD record
ord-34d64a82c71041f4970157da9d159bc6
Source dataset
uspto-grants-2015_12
Patent number
US09206182B2

Reaction notes

Loading…