Acetic Anhydride → 1-[2-(2,6-dichloroanilino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]allyl acetate

HRID 562427Notes

Reaction equation

HRID 562427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:29])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23]([OH:26])[CH:24]=[CH2:25])=[C:17]([CH3:27])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:28]=1.C(N(CC)CC)C.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[N:11]([CH3:29])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23]([O:26][C:37](=[O:39])[CH3:38])[CH:24]=[CH2:25])=[C:17]([CH3:27])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:28]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 110912672-(2,6-Dichloro-phenylamino)-7-(1-hydroxy-allyl)-1,6-dimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

Product 1

HCID 108743751-[2-(2,6-dichloroanilino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]allyl acetateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL round bottom flask equipped with a magnetic stir bar was added 2-(2,6-dichloro-phenylamino)-7-(1-hydroxy-allyl)-1,6-dimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one (0.175 g, 0.409 mmol), THF (5 mL), triethylamine (60 μL, 0.43 mmol) and acetic anhydride (1 mL). To the stirring suspension was then added N,N-dimethylaminopyridine (2 mg, 0.016 mmol). The reaction mixture became clear in 1 minute, and TLC analysis indicated that all starting material had been consumed. The reaction mixture was concentrated in vacuo and the residue was further purified by silica gel chromatography, eluting with methanol:dichloromethane (0-10%) to provide acetic acid 1-[2-(2,6-dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]-allyl ester (0.168 g, 87%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6+TFA) δ 11.42 (s, 1H), 7.80-7.76 (m, 4H), 7.57 (t, 1H, J=8.2 Hz), 6.34 (d, 1H, J=6.3 Hz), 6.21-6.13 (m, 1H), 5.41 (d, 1H, J=17.2 Hz), 5.33 (d, 1H, J=10.2 Hz), 4.25 (s, 3H), 2.33 (s, 3H), 2.12 (s, 3H); ESMS (m/z): found, 471.

Workup

  1. customTo a 100 mL round bottom flask equipped with a magnetic stir bar
  2. customhad been consumed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was further purified by silica gel chromatography
  5. washeluting with methanol

Sources & evidence

ORD record
ord-4c037ba7edb64505bb76cef2b3f74b68
Source dataset
uspto-grants-2011_11
Patent number
US08067395B2

Reaction notes

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