Acetic Anhydride → HCID 67608316, compound

HRID 1965216Notes

Reaction equation

HRID 1965216 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[NH:25][CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:40](=[O:42])[CH3:41])[CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:16])([CH3:17])[CH3:15])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 67606764HCID 67606764, compound

Product 1

HCID 67608316HCID 67608316, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of amine 84 (480 mg, 0.87 mmol) in DCM (8 mL) was treated with acetic anhydride (0.12 mL, 1.3 mmol) followed by DMAP (11 mg, 0.087 mmol). After 18 h, the solution was diluted with DCM, washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 86 (537 mg, 100%) as a white foam that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.11-6.99 (m, 1H), 6.89 (br s, 1H), 6.74-6.67 (m, 1H), 6.61-6.56 (m, 1H), 4.77-4.69 (m, 1H), 4.63-4.57 (m, 2H), 4.39 (d, J=6.3 Hz, 1H), 4.10-3.95 (m, 2H), 3.82-3.67 (m, 2H), 3.54-3.48 (m, 1H), 3.45-3.36 (m, 1H), 2.87-2.79 (m, 4H), 2.44-2.38 (m, 1H), 2.23-2.08 (m, 6H), 1.65 (s, 1H), 1.49 (s, 9H), 1.32 (d, J=6.9 Hz, 3H), 0.99 (s, 9H) ppm.

Workup

  1. washwashed successively with 1M HCl, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6173ecbdffe45bd9849afe37fbae03d
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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