Dimethylacetamide → HCID 25262476, compound

HRID 512998Notes

Reaction equation

HRID 512998 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[C:18]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]4[CH3:25])=[N:17][C:16]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]4[CH3:32])=[N:15][C:14]=3[N:33]=2)=[CH:6][C:5]=1OC.CC(N(C)C)=O.[CH2:43]([NH2:46])[CH2:44][NH2:45].CC(N(C)C)=O>C(N)CN>[CH3:32][C@H:27]1[CH2:28][O:29][CH2:30][CH2:31][N:26]1[C:16]1[N:17]=[C:18]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[C:13]2[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]4[C:3](=[O:2])[NH:46][CH2:43][CH2:44][NH:45][C:5]=4[CH:6]=3)=[N:33][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 59703453HCID 59703453, compoundHCID 131730547HCID 131730547, compound

Product 1

HCID 25262476HCID 25262476, compound

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

Procedure

A solution of 4-[2,4-bis-((S)-3-methyl-morpholin-4-yl)-pyrido[2,3-d]pyrimidin-7-yl]-2-methoxy-benzoic acid methyl ester (1 equiv) in ethylenediamine (0.35 M) was stirred at room temperature for 24 hours. DMA was added to the solution (ethylenediamine/DMA 1:1.25). The reaction vessel was sealed and exposed to microwave radiation (180° C., medium absorption setting) for 1hour. The reaction mixture was diluted with CH2Cl2 and extracted with water and washed with brine. The organic layer was dried with magnesium sulphate, filtered and concentrated in vacuo to yield a yellow solid which was then purified by preparative HPLC to give the desired product.

Workup

  1. customThe reaction vessel was sealed
  2. customexposed to microwave radiation (180° C., medium absorption setting) for 1hour
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. extractionextracted with water
  5. washwashed with brine
  6. dry with materialThe organic layer was dried with magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a yellow solid which
  10. customwas then purified by preparative HPLC

Sources & evidence

ORD record
ord-e27e36dacb5342fcb55b996c34653220
Source dataset
uspto-grants-2015_08
Patent number
US09102670B2

Reaction notes

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