Acetic Anhydride → HCID 46843752, compound

HRID 533769Notes

Reaction equation

HRID 533769 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:19]4[C:18]5[CH2:20][NH:21][CH2:22][CH2:23][C:17]=5[NH:16][C:15]=4[N:14]=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:24](OC(=O)C)(=[O:26])[CH3:25].C(N(CC)CC)C>ClCCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:19]4[C:18]5[CH2:20][N:21]([C:24](=[O:26])[CH3:25])[CH2:22][CH2:23][C:17]=5[NH:16][C:15]=4[N:14]=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66677885HCID 66677885, compound

Product 1

HCID 46843752HCID 46843752, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Indan-5-yl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (75 mg, 0.25 mmol), acetic anhydride (25 μL, 0.25 mmol), and triethylamine (102 μL, 0.74 mmol) were dissolved in 1,2-dichloroethane (2 mL), and stirred for 30 min at room temperature. The reaction was quenched with H2O, and the resulting material was filtered through an Extrelut column. The Extrelut column was washed with EtOAc, and the filtrate was concentrated. The crude material was purified via Biotage eluting with a gradient of 0 to 10% MeOH in DCM. Lyophilization of the purified product provided 64 (21 mg, 25% yield) as an oily residue. LC-MS (M+H=347, obsd.=347).

Workup

  1. customThe reaction was quenched with H2O
  2. filtrationthe resulting material was filtered through an Extrelut column
  3. washThe Extrelut column was washed with EtOAc
  4. concentrationthe filtrate was concentrated
  5. customThe crude material was purified via Biotage
  6. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-9ced995557dc476fab4bf517dda924e7
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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