Pyridine → HCID 58382315, compound

HRID 1628117Notes

Reaction equation

HRID 1628117 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]2[C:10]3[CH:16]=[C:15]([C:17]4[C:25]5[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=5)[N:19]([CH3:28])[CH:18]=4)[N:14]([CH2:29][OH:30])[C:11]=3[N:12]=[CH:13][C:8]2=[CH:7][N:6]=1.[CH3:31][C:32](OC(C)=O)=[O:33].N1C=CC=CC=1>C1COCC1.C([O-])(O)=O.[Na+]>[OH:30][CH2:29][N:14]1[C:11]2[N:12]=[CH:13][C:8]3[N:9]([C:5]([CH2:4][CH2:3][CH2:2][NH:1][C:32](=[O:33])[CH3:31])=[N:6][CH:7]=3)[C:10]=2[CH:16]=[C:15]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]([CH3:28])[CH:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic Anhydride2×HCID 58382104HCID 58382104, compound

Product 1

HCID 58382315HCID 58382315, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (1-(3-aminopropyl)-7-(5-methoxy-1-methyl-1H-indol-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-6-yl)methanol (0.116 g, 0.287 mmol) in THF (3 mL) at rt was added Ac2O (0.032 mL, 0.344 mmol) and pyridine (1.0 mL, 12.36 mmol). After about 10 min, additional Ac2O (0.027 mL, 0.287 mmol) was added. After about 15 min the mixture was diluted with aqueous NaHCO3 (10 mL) and extracted with EtOAc (20 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 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, 100%): LC/MS (Table 2, Method c) Rt=1.26 min; MS m/z 447 (M+H)+.

Workup

  1. extractionextracted with EtOAc (20 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbbd1d87c81942138053f5fc3d46bd49
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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