Acetic Anhydride → HCID 69220169, compound

HRID 272707Notes

Reaction equation

HRID 272707 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16].[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:19](=[O:21])[CH3:20])=[CH:5][C:4]=1[O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 69216512HCID 69216512, compound

Product 1

HCID 69220169HCID 69220169, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of Example 476B, acetic anhydride (20 mL), and 4-(dimethylamino)pyridine (722 mg, 5.9 mmol) in dichloroethane (150 mL) was stirred at room temperature for 2 hours. The reaction mixture was then concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was diluted with hexanes and stirred vigorously until a solid formed. The solid was filtered, rinsed with hexane, and dried under vacuum to produce 15 g (81% over 3 steps from Examples 476A-C) of the desired product. MS (ESI) m/e 334 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) □ 9.74 (s, 1H), 7.33 (d, J=2.7 Hz, 1H), 7.18 (dd, J=2.5, 8.7 Hz, 1H), 6.89 (d, J=8.8 Hz, 1H), 5.13 (s, 2H), 3.67-3.73 (m, 2H), 3.71 (s, 3H), 1.98 (s, 3H), 0.86-0.92 (m, 2H), -0.02 (s, 9H).

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe residue was diluted with hexanes
  8. customformed
  9. filtrationThe solid was filtered
  10. washrinsed with hexane
  11. customdried under vacuum

Sources & evidence

ORD record
ord-a6089568b6bb446782cfadf4fbcbe408
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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