Acetic Anhydride → HCID 46843749, compound

HRID 533767Notes

Reaction equation

HRID 533767 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:17]3[C:16]4[CH2:18][NH:19][CH2:20][CH2:21][C:15]=4[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(N(CC)CC)C>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:17]3[C:16]4[CH2:18][N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21][C:15]=4[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 46843675HCID 46843675, compound

Product 1

HCID 46843749HCID 46843749, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(3-Fluoro-phenyl)-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (15 mg, 0.05 mmol), acetic anhydride (53 μL, 0.05 mmol), and triethylamine (22 μL, 0.16 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 61 (3 mg, 15% yield) as an oily residue. LC-MS (M+H=325, obsd.=325).

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-2156284d2dab473782e29ce9e6433c3c
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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