Triethylamine → HCID 59020348, compound

HRID 970450Notes

Reaction equation

HRID 970450 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]([S:17]([CH3:20])(=[O:19])=[O:18])[C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)#[N:2].[Br:21][C:22]1[C:23](Cl)=[N:24][C:25]([Cl:28])=[N:26][CH:27]=1.C(N(CC)CC)C>C(O)C.Cl.C(#N)C.[Pt](=O)=O>[Br:21][C:22]1[C:23]([NH:2][CH2:1][CH2:3][CH2:4][CH2:5][N:6]([S:17]([CH3:20])(=[O:19])=[O:18])[C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=2)=[N:24][C:25]([Cl:28])=[N:26][CH:27]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 59020448HCID 59020448, compound

Product 1

HCID 59020348HCID 59020348, compound

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

460 mg (1.56 mmol) of N-{3-[(3-cyano-propyl)-methanesulfonyl-amino]-phenyl}-acetamide in 25 ml of ethanol and 0.5 ml of concentrated HCl are hydrogenated with use of 60 mg (0.26 mmol) of platinum(IV)oxide for 5 hours at room temperature under normal pressure. The batch is filtered and concentrated by evaporation. The residue that is obtained is mixed with a solution of 355 mg (1.56 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 15 ml of acetonitrile. 0.45 ml of triethylamine is added drop by drop, and it is stirred for 16 hours at room temperature. The batch is concentrated by evaporation, and the residue that is obtained is purified by chromatography (DCM/EtOH 95:5). 330 mg (0.67 mmol, corresponding to 43% of theory) of the product is obtained.

Workup

  1. filtrationThe batch is filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue that is obtained
  4. concentrationThe batch is concentrated by evaporation
  5. customthe residue that is obtained
  6. customis purified by chromatography (DCM/EtOH 95:5)
  7. custom330 mg (0.67 mmol, corresponding to 43% of theory) of the product is obtained

Sources & evidence

ORD record
ord-625ba3b82e844de79483f45cc9185d5e
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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