HCID 86641478, compound → {5-Chloro-1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[4,3-d]pyrimidin-3-yl}-acetic acid

HRID 472739Notes

Reaction equation

HRID 472739 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([Cl:19])=[N:16][CH:17]=[CH:18][C:11]=2[N:10]([CH2:20][C:21](=[O:34])[NH:22][C:23]2[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH3:31])=[CH:25][C:24]=2[O:32][CH3:33])[C:9]1=[O:35])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:19][C:15]1[C:12]2[C:13](=[O:14])[N:8]([CH2:7][C:6]([OH:36])=[O:5])[C:9](=[O:35])[N:10]([CH2:20][C:21](=[O:34])[NH:22][C:23]3[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH3:31])=[CH:25][C:24]=3[O:32][CH3:33])[C:11]=2[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 1

HCID 86641478HCID 86641478, compound2×

Product 1

HCID 59317708{5-Chloro-1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[4,3-d]pyrimidin-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a vial containing a solution of {5-Chloro-1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[4,3-d]pyrimidin-3-yl}-acetic acid tert-butyl ester (Intermediate T) (10.1 mg, 0.019 mmol) in DCM (1 ml), TFA (1 ml) is added. The reaction mixture is stirred at RT for 2 hours, transferred to a 10 ml round bottomed flask, diluted with a minimal amount of DCM and concentrated in vacuo. The residue is taken up in a minimal amount of DCM and concentrated in vacuo. This process is repeated once with DCM, twice with EtOAc, and once with MeOH, the solvent being concentrated in vacuo each time, finally giving the title compound.

Workup

  1. additionis added
  2. customtransferred to a 10 ml round bottomed flask
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated in vacuo
  5. concentrationonce with MeOH, the solvent being concentrated in vacuo each time

Sources & evidence

ORD record
ord-f4fcef4606b445939faef957f9cb1d05
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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