Dimethylformamide → HCID 71294279, compound

HRID 1019747Notes

Reaction equation

HRID 1019747 reaction equation
[NH2:1][C:2]1[C:25]([O:26][CH3:27])=[CH:24][C:5]([CH2:6][CH2:7][N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([Cl:28])[CH:3]=1.C1(O[C:36](=[O:45])[NH:37][C:38]2[CH:43]=[N:42][C:41](Cl)=[CH:40][N:39]=2)C=CC=CC=1.[CH3:46][N:47](C=O)C>>[Cl:28][C:4]1[CH:3]=[C:2]([NH:1][C:36]([NH:37][C:38]2[CH:43]=[N:42][C:41]([C:46]#[N:47])=[CH:40][N:39]=2)=[O:45])[C:25]([O:26][CH3:27])=[CH:24][C:5]=1[CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67468901HCID 67468901, compoundHCID 86678154HCID 86678154, compound

Product 1

HCID 71294279HCID 71294279, compoundYield 47%

Procedure

A solution of tert-butyl 4-amino-2-chloro-5-methoxyphenethyl(3-fluorobenzyl)-carbamate (0.3 g, 0.74 mmol) and phenyl-5-chloropyrazin-2-ylcarbamate (0.18 g, 0.74 mmol) in DMF (30 mL) was heated to 100° C. for 2 hours. The mixture was partitioned between water (200 mL) and EtOAc (50 mL) and the separated aqueous layer was extracted with EtOAc (50 mL). The combined organic extracts were washed with water (200 mL), brine (200 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 20-30% EtOAc in hexane to give the title compound (0.19 g, 47%) as a solid.

Workup

  1. customThe mixture was partitioned between water (200 mL) and EtOAc (50 mL)
  2. extractionthe separated aqueous layer was extracted with EtOAc (50 mL)
  3. washThe combined organic extracts were washed with water (200 mL), brine (200 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on neutral silica gel using 20-30% EtOAc in hexane

Sources & evidence

ORD record
ord-5260eac16e88480e8f1f4ca12626340a
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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