Acetic Anhydride → HCID 24900742, compound

HRID 1158753Notes

Reaction equation

HRID 1158753 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:19]([NH2:21])=[O:20])=[CH:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:15][CH2:16][NH2:17])[C:7]=2[N:18]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:22]([NH:17][CH2:16][CH2:15][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:5]=[C:4]([C:19]([NH2:21])=[O:20])[C:3]([NH2:2])=[N:18][C:7]1=2)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 66676052HCID 66676052, compound

Product 1

HCID 24900742HCID 24900742, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-9-(2-aminoethyl)-9H-pyrido[2,3-b]indole-3-carboxamide (16, 50.0 mg, 0.186 mmol) in pyridine (2 mL) was added DMAP (23.0 mg, 0.188 mmol) and acetic anhydride (23 μL, 0.243 mmol). The reaction was stirred at RT under an atmosphere of argon. After 1 h, the reaction was concentrated and the crude product was purified by HPLC (Phenomenex Luna 15 μm C18, aqueous NH4OAc/CH3CN) to yield 9-[2-(acetylamino)ethyl]-2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (22, 11 mg, 19%). NH4OAc standard conditions. DAD Retention time =5.18 min. M+H=312. 1H NMR (300 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.01 (t, J=5.7 Hz, 1H), 7.80 (d, J=7.5 Hz, 1H), 7.58 (br s, 2H), 7.46 (d, J=8.1 Hz, 1H), 7.33 (t, J=8.1 Hz, 1H), 7.18 (t, J=7.5 Hz, 1H), 4.31 (t, J=6.0 Hz, 2H), 3.41 (q, J=6.0 Hz, 2H), 1.71 (s, 3H).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe crude product was purified by HPLC (Phenomenex Luna 15 μm C18, aqueous NH4OAc/CH3CN)

Sources & evidence

ORD record
ord-f6834cb183b94fd08c8bd44b6d267dde
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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