Diisopropylethylamine → 6-chloro-N-1H-indazol-5-ylpyrimidine-4-carboxamide

HRID 1946672

Reaction equation

HRID 1946672 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.ClC1N=CN=C(C(NC2C=CC(O)=CC=2)=O)C=1.[NH2:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][N:33]=[CH:32]2.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:28][C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[NH:34][N:33]=[CH:32]3)=[O:9])[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 880121H-Indazol-5-amineHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

Product 1

HCID 594468806-chloro-N-1H-indazol-5-ylpyrimidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 6-chloropyrimidine-4-carbonyl chloride in DCM (60 mL), obtained as described above for Intermediate 7, step 1 (798 mg; 4.51 mmol) was added dropwise, during a period of 30 minutes, a solution of 5-aminoindazole (Aldrich, 500 mg; 3.76 mmol) and DIEA (1.29 ml; 7.51 mmol) in dry DMF (5 mL). At the end of addition the reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. A white precipitate separated from the organic phase. It was filtered and dried in vacuo to afford the title compound as a beige solid.

Workup

  1. customobtained
  2. additionwas added dropwise, during a period of 30 minutes
  3. additionAt the end of addition the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted with EtOAc
  7. customA white precipitate separated from the organic phase
  8. filtrationIt was filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d28216013b0a4c008eef597759c5c7f0
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Linked notes

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