HCID 66656291, compound → HCID 56602346, compound

HRID 2367740Notes

Reaction equation

HRID 2367740 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH:12][C:13]([C:15]3[CH:16]=[C:17]([CH:51]=[CH:52][CH:53]=3)[CH2:18][NH:19][C:20]([C:22]3[S:23][C:24]([C:27]4[CH:28]=[N:29][N:30](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:31]=4)=[CH:25][CH:26]=3)=[O:21])=[O:14])=[CH:7][CH:8]=2)[CH2:3]1>N1C=CC=CC=1.Cl.CO>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH:12][C:13]([C:15]3[CH:16]=[C:17]([CH:51]=[CH:52][CH:53]=3)[CH2:18][NH:19][C:20]([C:22]3[S:23][C:24]([C:27]4[CH:28]=[N:29][NH:30][CH:31]=4)=[CH:25][CH:26]=3)=[O:21])=[O:14])=[CH:7][CH:8]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 66656291HCID 66656291, compound

Product 1

HCID 56602346HCID 56602346, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10176127Pyridinium chlorideSolvent

Procedure

Heat a solution of 5-(1-trityl-1H-pyrazol-4-yl)-thiophene-2-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (167 mg, 0.234 mmol) in 10% pyridine/HCl in MeOH (50 mL) at 50° C. overnight. Cool the reaction to rt, concentrate, and purify the residue by prep-HPLC (10% to 90%, CH3CN/water). Further purify the residue through a short silica plug to remove baseline impurity affording desired product 5-(1H-pyrazol-4-yl)-thiophene-2-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (68 mg, 0.097 mmol). MS, electrospray 472.2 (M+H), rt 0.94 min.

Workup

  1. temperatureCool
  2. customthe reaction to rt
  3. concentrationconcentrate
  4. custompurify the residue by prep-HPLC (10% to 90%, CH3CN/water)
  5. customFurther purify the residue through a short silica plug
  6. customto remove baseline impurity

Sources & evidence

ORD record
ord-80173193bf8141b59a614c4df2b299cd
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

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