Ammonium Hydroxide → HCID 58381979, compound

HRID 1628118Notes

Reaction equation

HRID 1628118 reaction equation
OC[N:3]1[C:7]2[N:8]=[CH:9][C:10]3[N:11]([C:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[N:13][CH:14]=3)[C:6]=2[CH:5]=[C:4]1[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]([CH3:33])[CH:23]=1.[NH4+].[OH-]>CO>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:33])[CH:23]=[C:22]2[C:4]1[NH:3][C:7]2[N:8]=[CH:9][C:10]3[N:11]([C:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[N:13][CH:14]=3)[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 58382315HCID 58382315, compound

Product 1

HCID 58381979HCID 58381979, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(3-(6-(hydroxymethyl)-7-(5-methoxy-1-methyl-1H-indol-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)propyl)acetamide (0.128 g, 0.287 mmol) in MeOH (3 mL) at rt was added 30 wt % aqueous NH4OH (0.37 mL, 2.87 mmol) and the mixture was heated to about 60° C. for about 30 min. The mixture was cooled to about 0° C. and was sonicated to provide a solid which was collected by filtration. The solid material was taken up in EtOAc (15 mL) and washed with water (10 mL). The organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by a 12 g silica column eluting with 0 to 10% MeOH in DCM to provide N-(3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)propyl)acetamide (0.025 g, 21%): LC/MS (Table 2, Method c) Rt=1.25 min; MS m/z 417 (M+H)+. Syk IC50=A

Workup

  1. temperatureThe mixture was cooled to about 0° C.
  2. customwas sonicated
  3. customto provide a solid which
  4. filtrationwas collected by filtration
  5. washwashed with water (10 mL)
  6. dry with materialThe organics were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by a 12 g silica column
  10. washeluting with 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-0cb8829ef7cc423da21e3b3a793ed572
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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