Acetic Anhydride → HCID 86710198, compound

HRID 2284434Notes

Reaction equation

HRID 2284434 reaction equation
[C:1]([O:4][CH2:5][O:6][C:7](=[O:32])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:24]=[N:23][C:22]3[C:21]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[N:20][C:19]([Cl:31])=[N:18][C:17]=3[CH:16]=2)[CH:10]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl>[C:1]([O:4][CH2:5][O:6][C:7](=[O:32])[N:8]([C:40](=[O:42])[CH3:41])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:24]=[N:23][C:22]3[C:21]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)=[N:20][C:19]([Cl:31])=[N:18][C:17]=3[CH:16]=2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 86710195HCID 86710195, compound

Product 1

HCID 86710198HCID 86710198, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 mL round bottom flask, (((3-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)phenyl)carbamoyl)oxy)methyl acetate (1.0 g, 0.0022 mol), triethylamine (0.6 mL, 0.0044 mol) N,N-dimethylpyridin-4-amine (0.0054 g, 0.000044 mol) and DCM (25 mL) were added. To the same flask was added acetic anhydride (2.67 g, 0.0264 mol). The reaction was continued at room temperature for 18 hour. Additional acetic anhydride (1.63 g, 0.0161 mol) was then added to the reaction mixture. The reaction was further continued at room temperature for 24 hours. The reaction mixture was diluted with DCM. The organic layer was washed with water, brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to provide the title compound (0.97 g, 83%). 1H NMR (400 MHz, DMSO-d6): δ 9.14 (d, J=2.0 Hz, 1H), 8.32 (d, J=2.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.87 (s, 1H), 7.61 (t, J=7.6 Hz, 1H), 7.53 (dd, J′=7.6 Hz, J″=0.8 Hz, 1H), 5.66 (s, 2H), 4.65-3.97 (br s, 4H), 3.80 (t, J=4.8 Hz, 4H), 2.55 (s, 3H), 2.03 (s, 3H). LC-MS (ESI): Calculated mass: 499.13; Observed mass [M+H]+: 499.8 (RT: 1.52 min).

Workup

  1. waitThe reaction was further continued at room temperature for 24 hours
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-be57f9b912cf42a18d9fe79dd04b23fd
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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