Chloromethyl chloroformate → HCID 86710194, compound

HRID 2284432Notes

Reaction equation

HRID 2284432 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=3)[NH2:15])=[CH:8][C:6]=2[N:7]=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.Cl[C:42]([O:44][CH2:45][Cl:46])=[O:43]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]([NH:15][C:42](=[O:43])[O:44][CH2:45][Cl:46])[CH:16]=[CH:17][CH:18]=3)=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 62754Chloromethyl chloroformateHCID 88675Proton spongeHCID 86710186HCID 86710186, compound

Product 1

HCID 86710194HCID 86710194, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a 100 mL round bottom flask, 3-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)aniline (1.0 g, 0.0029 mol), 1,8-bis(dimethylamino)naphthalene (0.626 g, 0.0029 mol) and chloroform (60 mL) were added. The reaction mixture was cooled in an ice bath. To the same flask was added chloromethyl chloroformate (0.377 g, 0.0029 mol) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with chloroform, washed with water and brine. The organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to provide the title compound as a yellow solid (1.25 g, 98.4%). 1H NMR (400 MHz, DMSO-d6): δ 10.41 (br s, 1H), 9.07 (d, J=2.0 Hz, 1H), 8.22 (d, J=2.0 Hz, 1H), 7.94 (br s, 1H), 7.62-7.51 (m, 3H), 6.01 (s, 2H), 4.98-3.98 (br s, 4H), 3.81 (t, J=4.4 Hz, 4H). LC-MS (ESI): Calculated mass: 433.07; Observed mass [M+H]+: 433.8 (RT: 1.63 min).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-52f23cd2f5e54d3c84ab7a8ae260f383
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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