2,4,6-Trimethylpyridine → HCID 56672028, compound

HRID 1914814Notes

Reaction equation

HRID 1914814 reaction equation
[C:1]([NH:5][C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]([OH:13])=O)[CH2:7]1)(=[O:4])[CH2:2][CH3:3].ClC(N(C)C)=C(C)C.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:34]([CH3:35])[C:33]3[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=3[N:31]=2)=[CH:26][CH:25]=1.N1C(C)=CC(C)=CC=1C>C1COCC1.C(Cl)Cl>[CH3:22][N:23]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:34]([CH3:35])[C:33]3[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=3[N:31]=2)=[CH:26][CH:25]=1)[C:11]([C@@H:8]1[CH2:9][CH2:10][C@H:6]([NH:5][C:1](=[O:4])[CH2:2][CH3:3])[CH2:7]1)=[O:13]

Participants

7

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 13713019HCID 13713019, compoundHCID 67112454HCID 67112454, compound

Product 1

HCID 56672028HCID 56672028, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

100.0 mg (0.54 mmol) (1R,3S)-3-Propionylamino-cyclopentanecarboxylic acid (educt IV.1) and 78.6 μL (0.59 mmol) 1-chloro-N,N,2-trimethyl-propenylamine are stirred in 5 mL dry THF at RT for 1 hour. Then this mixture is given to a mixture of 128.1 mg (0.54 mmol) N-methyl-N-[4-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-amine (educt III.1.a) and 107.0 μL (0.81 mmol) 2,4,6-collidine in DCM at RT. The mixture is stirred over night. The solvent is evaporated. The residue is taken up with water and extracted with DCM. The organic phase is dried and the solvent is evaporated. The residue is triturated with diethyl ether, filtered off and dried.

Workup

  1. customThe solvent is evaporated
  2. extractionextracted with DCM
  3. customThe organic phase is dried
  4. customthe solvent is evaporated
  5. customThe residue is triturated with diethyl ether
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-78f86ecdc6dc4d908d0ac1b79d39b431
Source dataset
uspto-grants-2013_12
Patent number
US08614238B2

Reaction notes

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