Acetic Anhydride → HCID 46843680, compound

HRID 533762Notes

Reaction equation

HRID 533762 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([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:9][C:4]=2[O:3][CH2:2]1.[C:24](OC(=O)C)(=[O:26])[CH3:25].C(N(CC)CC)C>ClCCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([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:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 46843679HCID 46843679, compound

Product 1

HCID 46843680HCID 46843680, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Benzo[1,3]dioxol-5-yl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (50 mg, 0.16 mmol), acetic anhydride (18 μL, 0.19 mmol), and triethylamine (67 μL, 0.49 mmol) were dissolved in 1,2-dichloroethane (2 mL), and stirred overnight at room temperature. The reaction mixture was added directly to a Biotage column. The crude product was purified via Biotage eluting with a gradient of 0 to 10% MeOH in DCM. Lyophilization of the purified product provided 56 (25 mg, 44% yield) as a tan powder. LC-MS (M+H=351, obsd.=351).

Workup

  1. additionThe reaction mixture was added directly to a Biotage column
  2. customThe crude product was purified via Biotage
  3. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-1acf6e0f309342a99ec7c4e0f0fa4ab7
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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