Hydrochloric Acid → HCID 135923524, compound

HRID 2076820Notes

Reaction equation

HRID 2076820 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][O:11][CH2:12][C:13]([NH:15][C:16]([C:18]2[C:23](Cl)=[N:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[NH:14])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[K+].[K+].O.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][O:11][CH2:12][C:13]2[NH:15][C:16](=[O:17])[C:18]3[C:23](=[N:22][CH:21]=[CH:20][N:19]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 141215261HCID 141215261, compound

Product 1

HCID 135923524HCID 135923524, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of crude 3-chloro-pyrazine-2-carboxylic acid{2-[2-(3-chloro-4-fluoro-phenyl)-ethoxy]-1-imino-ethyl}-amide (300 mg) and K2CO3 (223 mg, 1.616 mmol) in DMF (3 ml) was heated to 100° C. for 2 h. Then water was added and the pH was adjusted to 5 by addition of 0.1 N HCl. The brown precipitate that formed was filtered off, washed with water and dried. The resulting solid was triturated with Et2O. The remaining solid was filtered off, washed with a small amount of Et2O and dried to give the title compound as a light brown solid (122 mg, 45%). MS: m/e=335.2 [M+H+].

Workup

  1. customThe brown precipitate that formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. customdried
  5. customThe resulting solid was triturated with Et2O
  6. filtrationThe remaining solid was filtered off
  7. washwashed with a small amount of Et2O
  8. customdried

Sources & evidence

ORD record
ord-35a7f751ed534be99d0549e2f2fcabae
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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