Acetic Anhydride → HCID 46843683, compound

HRID 533765Notes

Reaction equation

HRID 533765 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH2:13][CH2:12][NH:11][CH2:10][C:9]=3[C:5]=2[C:4]([NH:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=2)=[CH:3][CH:2]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(CC)CC)C>ClCCCl>[CH:16]1[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[CH:23]=[CH:24][C:15]=1[NH:14][C:4]1[C:5]2[C:9]3[CH2:10][N:11]([C:25](=[O:27])[CH3:26])[CH2:12][CH2:13][C:8]=3[NH:7][C:6]=2[N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66677889HCID 66677889, compound

Product 1

HCID 46843683HCID 46843683, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-(5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (75 mg, 0.24 mmol), acetic anhydride (25 μL, 0.24 mmol), and triethylamine (98 μL, 0.71 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 59 (22 mg, 26% yield) as a tan powder. LC-MS (M+H=361, obsd.=361).

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-eace92e413f342c9973c6fc000abe934
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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