Acetic Anhydride → HCID 46843681, compound

HRID 533763Notes

Reaction equation

HRID 533763 reaction equation
[C:1]1([NH:11][C:12]2[C:20]3[C:19]4[CH2:21][NH:22][CH2:23][CH2:24][C:18]=4[NH:17][C:16]=3[N:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(CC)CC)C>ClCCCl>[C:1]1([NH:11][C:12]2[C:20]3[C:19]4[CH2:21][N:22]([C:25](=[O:27])[CH3:26])[CH2:23][CH2:24][C:18]=4[NH:17][C:16]=3[N:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66677449HCID 66677449, compound

Product 1

HCID 46843681HCID 46843681, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Naphthalen-1-yl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (40 mg, 0.13 mmol), acetic anhydride (12 μL, 0.13 mmol), and triethylamine (53 μL, 0.38 mmol) were dissolved in 1,2-dichloroethane (2 mL), and stirred for 3 h 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 57 (10 mg, 22% yield) as a tan powder. LC-MS (M+H=357, obsd.=357).

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-23317b123af047d498f77b75f9d0e489
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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