Acetic Anhydride → HCID 49764533, compound

HRID 1022503Notes

Reaction equation

HRID 1022503 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:15](=[O:26])[N:14]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[C:13]2=[O:38].CCN(CC)CC>C(Cl)Cl>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[O:34][CH3:35])[CH2:27][N:14]1[C:13](=[O:38])[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([CH2:9][NH:8][C:1](=[O:3])[CH3:2])[CH:11]=2)[N:16]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:15]1=[O:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 667329246-(aminomethyl)-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 49764533HCID 49764533, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.066 g of acetic anhydride is added at 0° C. to a solution of 0.23 g of the compound obtained in Step 12.2 and 0.11 g of Et3N in 5 ml of DCM. The mixture is stirred at room temperature for 2 hours. The organic phase is washed with saturated NH4Cl solution, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (99/1, v/v) to (95/5, v/v) to give 0.195 g of the expected product.

Workup

  1. washThe organic phase is washed with saturated NH4Cl solution
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with a DCM/MeOH mixture from (99/1

Sources & evidence

ORD record
ord-70aaac32ec6041c8bac20cae1e36da57
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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