Carbonate Ion → HCID 69196533, compound

HRID 2221314Notes

Reaction equation

HRID 2221314 reaction equation
[C:1](=[O:4])([O-])[O-:2].[NH2:5][C:6]1[C:7]([CH3:19])=[C:8](Br)[C:9]2[O:14][C:13]([CH3:16])([CH3:15])[CH:12]=[CH:11][C:10]=2[CH:17]=1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[C:1](=[O:4])([OH:2])[NH2:5].[NH2:5][C:6]1[C:7]([CH3:19])=[CH:8][C:9]2[O:14][C:13]([CH3:15])([CH3:16])[CH:12]=[CH:11][C:10]=2[CH:17]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 81531DiisopropylethylamineHCID 59711047HCID 59711047, compound

Product 1

HCID 69196533HCID 69196533, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

After a carbonate resin (0.80 mmol/g, 10 g, 8.0 mmol) of formula 2 was mixed with dimethylacetamide (DMA, 50 mL) by shaking at room temperature for 10 min, 6-amino-8-bromo-2,2,7-trimethyl-2H-benzopyran (4.29 g, 16.0 mmol) and diisopropylethyl amine (DIPEA; 5.17 mg, 40.0 mmol) were successively added thereto and mixed by shaking at 25° C. for 15 hrs. After the reaction was completed, the reaction mixture was subjected to filtration and repeatedly washed with DMF, DCM, DCM/MeOH and MeOH, to obtain a solid resin (Formula 4-10; 12.2 g). (ATR-FTIR; carbamate: 1725 cm−1)

Workup

  1. additionmixed
  2. stirringby shaking at 25° C. for 15 hrs
  3. filtrationthe reaction mixture was subjected to filtration
  4. washrepeatedly washed with DMF, DCM, DCM/MeOH and MeOH

Sources & evidence

ORD record
ord-dea60d228fd4492ab198df240d2542ba
Source dataset
uspto-grants-2008_05
Patent number
US07368575B2

Reaction notes

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