Acetic Anhydride → HCID 24900742, compound

HRID 421663Notes

Reaction equation

HRID 421663 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-302dcc4fe62644fda9c9ebd9639ecdc4
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

Loading…