HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 4-[2-(Cyclopropyl-methyl-amino)-thiazol-4-yl]-benzoic acid

HRID 606610
Notes
Print preview

Reaction equation

HRID 606610 reaction equation
[CH:1]1([NH:4][C:5]2[S:6][CH:7]=[C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=3)[N:9]=2)[CH2:3][CH2:2]1.CI.[C:21](=O)([O-])[O-].[K+].[K+].[Li+].[OH-].Cl>CN(C=O)C.CO.C1COCC1>[CH:1]1([N:4]([CH3:21])[C:5]2[S:6][CH:7]=[C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=3)[N:9]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 598073364-[2-(Cyclopropylamino)-1,3-thiazol-4-yl]benzoic acid

Product 1

HCID 582569894-[2-(Cyclopropyl-methyl-amino)-thiazol-4-yl]-benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Cyclopropylamino-thiazol-4-yl)benzoic acid (1.98 mmol), methyliodide (4.36 mmol) and potassium carbonate were mixed in DMF (20 mL) and stirred for 72 hours at room temperature. The mixture was concentrated to dryness and partitioned between dichloromethane and water. The organic layer was dried (MgSO4) and concentrated to dryness. This solid was mixed with THF (4 mL), methanol (2 mL) and 1N LiOH (3 mmol) and heated to 50° C. for 1 hour. The mixture was then cooled to room temperature and 1N HCl was added until pH 4. The mixture was concentrated in vacuo, then the obtained residue was redissolved in dichloromethane-methanol and concentrated onto silica. Flash chromatography of the residue (silica gel, dichloromethane-methanol) gave the title compound as an off-white solid (0.1 g), m/z=275.0 in MS ES+, which was characterised by hplc and MS.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated to dryness
  5. temperatureheated to 50° C. for 1 hour
  6. temperatureThe mixture was then cooled to room temperature
  7. concentrationThe mixture was concentrated in vacuo
  8. dissolutionthe obtained residue was redissolved in dichloromethane-methanol
  9. concentrationconcentrated onto silica

Sources & evidence

ORD record
ord-0dd8a922a81f4b33a48f7af3125d1bd1
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915300B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes