N-bromobutanimide → HCID 69586344, compound

HRID 723412Notes

Reaction equation

HRID 723412 reaction equation
[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:17])=[CH:16][N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:6]([O:25][CH2:26][CH2:27][O:28][CH3:29])[C@H:5]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:3])[CH3:2].C1C(=O)N([Br:43])C(=O)C1>C(O)C>[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:17])=[C:16]([Br:43])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:6]([O:25][CH2:26][CH2:27][O:28][CH3:29])[C@H:5]1[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69586503HCID 69586503, compound

Product 1

HCID 69586344HCID 69586344, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a of 0° C. cooled solution of 0.40 g (0.83 mmol) (7R,8R,9R)-10-acetyl-8-(2-methoxyethoxy)-2-methyl-9-phenyl-7-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine in ethanol (5 ml) is added 0.15 g (0.83 mmol) NBS and the mixture is stirred for 1 h. Afterwards the reaction is quenched by adding of saturated aqueous sodium hydrogen carbonate solution and it is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (ether/triethylamine: 95/5) to provide 0.30 g (0.53 mmol/65%) of the title compound as an amorphous solid. 1H-NMR (200 MHz, [D6] DMSO): δ=0.96 (s, 9H), 2.09(s, 3H), 2.42(s, 3H), 3.23(s, 3H), 3.40–3.53 (m, 2H), 3.69–3.98 (m, 2H), 4.23(t, 1H), 5.75 (d, 1H), 6.02 (s, 1H), 6.80(d, 1H), 7.16(s, 5H), 8.18(d, 1H).

Workup

  1. customAfterwards the reaction is quenched
  2. additionby adding of saturated aqueous sodium hydrogen carbonate solution and it
  3. extractionis extracted twice with dichloromethane
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography (ether/triethylamine: 95/5)

Sources & evidence

ORD record
ord-bb739467b5d84d819a3180aff04af6f9
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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