Trifluoroacetic acid → HCID 53247621, compound

HRID 1628122Notes

Reaction equation

HRID 1628122 reaction equation
[P:1]([O:13][CH2:14][N:15]1[C:19]2=[N:20][CH:21]=[C:22]3[CH:26]=[N:25][N:24]([CH3:27])[C:23]3=[C:18]2[CH:17]=[C:16]1[C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]([CH3:39])[CH:29]=1)([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[P:1]([OH:3])([OH:8])([O:13][CH2:14][N:15]1[C:19]2=[N:20][CH:21]=[C:22]3[CH:26]=[N:25][N:24]([CH3:27])[C:23]3=[C:18]2[CH:17]=[C:16]1[C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]([CH3:39])[CH:29]=1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58382025HCID 58382025, compound

Product 1

HCID 53247621HCID 53247621, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl (7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methylpyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-6(1H)-yl)methyl phosphate (0.486 g, 0.878 mmol) was dissolved in DCM (10 mL) then TFA (1.00 mL, 13.0 mmol) was added. The mixture was stirred 10 min then concentrated under reduced pressure. The material was dissolved in DMF (12 mL) and the material was purified by preparative reverse phase HPLC (Table 2, Method i). The fractions containing the title compound were collected then concentrated under reduced pressure to remove most of the MeCN. The solid was collected by filtration and washed with water (0.5 mL). The solid was dried to constant weight at about 60° C. under vacuum to give (7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methylpyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-6(1H)-yl)methyl dihydrogen phosphate (0.165 g, 43%): LC/MS (Table 2, Method a) Rt=1.58 min; MS m/z 442 (M+H)+. Syk IC50=C.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe material was dissolved in DMF (12 mL)
  3. customthe material was purified by preparative reverse phase HPLC (Table 2, Method i)
  4. additionThe fractions containing the title compound
  5. customwere collected
  6. concentrationthen concentrated under reduced pressure
  7. customto remove most of the MeCN
  8. filtrationThe solid was collected by filtration
  9. washwashed with water (0.5 mL)
  10. customThe solid was dried to constant weight at about 60° C. under vacuum

Sources & evidence

ORD record
ord-6555c94a3ed345178b451f6090b1116b
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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