Acetic Acid → HCID 86710195, compound

HRID 2284433Notes

Reaction equation

HRID 2284433 reaction equation
Cl[CH2:2][O:3][C:4](=[O:29])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:18]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:17][C:16]([Cl:28])=[N:15][C:14]=3[CH:13]=2)[CH:7]=1.[C:30]([OH:33])(=[O:32])[CH3:31]>C(Cl)(Cl)Cl>[C:30]([O:33][CH2:2][O:3][C:4](=[O:29])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:18]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[N:17][C:16]([Cl:28])=[N:15][C:14]=3[CH:13]=2)[CH:7]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86710194HCID 86710194, compound

Product 1

HCID 86710195HCID 86710195, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 100 mL round bottom flask, chloromethyl(3-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)phenyl)carbamate (1.2 g, 0.0028 mol) and acetic acid (20 mL) were added. To the reaction mixture was added mercuric acetate (0.968 g, 0.0031 mol) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with chloroform and washed with water. The organic layer was washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to provide the title compound as a yellow solid (1.1 g, 87%). 1H NMR (400 MHz, DMSO-d6): δ 10.25 (br s, 1H), 9.05 (d, J=1.6 Hz, 1H), 8.19 (d, J=1.2 Hz, 1H), 7.93 (s, 1H), 7.59-7.48 (m, 3H), 5.77 (s, 2H), 4.64-3.98 (br s, 4H), 3.81 (t, J=4.4 Hz, 4H), 2.10 (s, 3H). LC-MS (ESI): Calculated mass: 457.12; Observed mass [M+H]+: 457.9 (RT: 1.57 min).

Workup

  1. washwashed with water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d1562696c38d4645a2b68e0cb3401ea4
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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