Trifluoroacetic acid → HCID 58382044, compound

HRID 1628123Notes

Reaction equation

HRID 1628123 reaction equation
[P:1]([O:13][CH2:14][N:15]1[C:19]2[N:20]=[CH:21][C:22]3[N:23]([C:24]([CH3:27])=[N:25][CH:26]=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[N:23]([C:24]([CH3:27])=[N:25][CH:26]=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 58382091HCID 58382091, compound

Product 1

HCID 58382044HCID 58382044, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl (7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-6-yl)methyl phosphate (0.2 g, 0.361 mmol) was dissolved in DCM (5 mL) then TFA (0.2 mL, 2.60 mmol) was added. After about 20 min at rt the reaction mixture was concentrated under reduced pressure. The material was dissolved in DMF (7.5 mL) then the material was purified by preparative reverse phase HPLC (Table 2, Method i). The fractions were collected and concentrated under reduced pressure to remove most or all of the MeCN. The solid was collected by filtration and dried under vacuum to a constant weight at about 60° C. to provide (7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-6-yl)methyl dihydrogen phosphate (0.065 g, 41%): LC/MS (Table 2, Method a) Rt=1.42 min; MS m/z 442 (M+H)+.

Workup

  1. concentrationAfter about 20 min at rt the reaction mixture was concentrated under reduced pressure
  2. dissolutionThe material was dissolved in DMF (7.5 mL)
  3. customthe material was purified by preparative reverse phase HPLC (Table 2, Method i)
  4. customThe fractions were collected
  5. concentrationconcentrated under reduced pressure
  6. customto remove most
  7. filtrationThe solid was collected by filtration
  8. customdried under vacuum to a constant weight at about 60° C.

Sources & evidence

ORD record
ord-2b7421d472da46d3a1cec5eb2e2f3c2c
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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