Acetic Anhydride → HCID 59731987, compound

HRID 2378607Notes

Reaction equation

HRID 2378607 reaction equation
CS(O)(=O)=O.[O:6]=[C:7]1[N:20]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:19][C:11]2[C:12]3[CH:13]=[N:14][NH:15][C:16]=3[CH:17]=[CH:18][C:10]=2[CH2:9][C@H:8]1[NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C.[C:45](OC(=O)C)(=[O:47])[CH3:46].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:45]([N:24]1[CH2:25][CH2:26][CH:21]([N:20]2[C:7](=[O:6])[C@H:8]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:9][C:10]3[CH:18]=[CH:17][C:16]4[NH:15][N:14]=[CH:13][C:12]=4[C:11]=3[CH2:19]2)[CH2:22][CH2:23]1)(=[O:47])[CH3:46]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 86604790HCID 86604790, compound

Product 1

HCID 59731987HCID 59731987, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-benzyl 8-oxo-9-(piperidin-4-yl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate methanesulfonate (100 mg, 0.19 mmol) was dissolved in a mixture of dichloromethane (4 mL) and triethylamine (500 μL, 3.6 mmol). Acetic anhydride (500 μL, 5.3 mmol) was added to the mixture. Reaction stirred at room temperature overnight. Reaction mixture was washed successively 1× water, 2× 1N hydrochloric acid, 2× 1N sodium hydroxide, and 1× brine. Organic was dried (magnesium sulfate), and filtered. Filtrate was concentrated in vacuo. Residue was treated with methanol (3 mL). Potassium carbonate (40 mg, 0.29 mmol) was added to the mixture. Reaction stirred at room temperature for 2 hours. Reaction was quenched with 1N hydrochloric acid (6 mL). Methanol was removed from the mixture in vacuo. Remaining aqueous mixture was made basic with sodium bicarbonate. Mixture was extracted with ethyl acetate. Organic layer was dried (magnesium sulfate), filtered and concentrated. Title compound was obtained as yellow solid in 43% yield. MS m/e (M+H)+=476.

Workup

  1. customReaction
  2. customReaction mixture
  3. washwas washed successively 1× water, 2× 1N hydrochloric acid, 2× 1N sodium hydroxide, and 1× brine
  4. dry with materialOrganic was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationFiltrate was concentrated in vacuo
  7. additionResidue was treated with methanol (3 mL)
  8. customReaction
  9. stirringstirred at room temperature for 2 hours
  10. customReaction
  11. customwas quenched with 1N hydrochloric acid (6 mL)
  12. customMethanol was removed from the mixture in vacuo
  13. extractionMixture was extracted with ethyl acetate
  14. dry with materialOrganic layer was dried (magnesium sulfate)
  15. filtrationfiltered
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-12344e49fab542338acacd76b67e491e
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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