Ammonium Chloride → HCID 58382382, compound

HRID 1628070Notes

Reaction equation

HRID 1628070 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]3[C:12]([CH3:15])=[N:13][CH:14]=[C:9]3[CH:8]=[N:7][C:6]=2[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=1)[CH3:2].[CH3:33][Mg]Cl.[NH4+].[Cl-]>C1COCC1.O.CCOC(C)=O>[CH2:1]([C:3]1[C:11]2[N:10]3[C:12]([CH3:15])=[N:13][CH:14]=[C:9]3[CH:8]=[N:7][C:6]=2[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([OH:32])([CH3:33])[CH3:31])=[CH:28][CH:29]=1)[CH3:2]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 58382024HCID 58382024, compoundHCID 178418332HCID 178418332, compound4×

Product 1

HCID 58382382HCID 58382382, compoundYield 113.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-(8-Ethyl-1-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-7-yl)phenyl)ethanone (0.092 g, 0.205 mmol, Preparation #W.1) in THF (5 mL) was cooled to about −20° C. and MeMgCl (3.0 M in THF, 0.1 mL, 0.3 mmol) was added. After about 5 min MeMgCl (3.0 M in THF, 0.1 mL, 0.3 mmol) was added then the mixture was warmed to about 0° C. MeMgCl (3.0 M in THF, 0.2 mL, 0.6 mmol) was added and the mixture was allowed to warm to about 15° C. over about 2 h. MeMgCl (3.0 M in THF, 0.2 mL, 0.600 mmol) was added to THF (3 mL) and the solution was added to the mixture portion-wise. An aqueous solution of NH4Cl (4 mL) was added slowly. The mixture was diluted with water (20 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer was extracted with EtOAc (15 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 2-(4-(8-ethyl-1-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-7-yl)phenyl)propan-2-ol (0.108 g, 113%): LC/MS (Table 2, Method a) Rt=2.96 min.; MS m/z 465 (M+H)+.

Workup

  1. temperatureto warm to about 15° C. over about 2 h
  2. additionthe solution was added to the mixture portion-wise
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (15 mL)
  5. dry with materialThe combined organics were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22978f52ac304071922837e74cf4353a
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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