Triethylamine → HCID 178426950, compound

HRID 2352928Notes

Reaction equation

HRID 2352928 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]=[C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([C:22]4[CH:23]=[C:24]([NH:28][C:29]([C:31]5[N:32]([CH3:37])[N:33]=[C:34]([CH3:36])[CH:35]=5)=[O:30])[CH:25]=[CH:26][CH:27]=4)=[O:21])=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:38])=[CH:5][CH:4]=1.Cl.[CH3:40][N:41]([CH2:43][C:44](Cl)=[O:45])[CH3:42].C(N(CC)CC)C>CN(C=O)C>[CH3:37][N:32]1[C:31]([C:29]([NH:28][C:24]2[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=2)[C:20]([C:16]2[CH:15]=[C:14]3[C:19]([C:11](=[CH:10][NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][O:1][C:44](=[O:45])[CH2:43][N:41]([CH3:42])[CH3:40])=[CH:8][CH:7]=4)[C:12](=[O:38])[NH:13]3)=[CH:18][CH:17]=2)=[O:21])=[O:30])=[CH:35][C:34]([CH3:36])=[N:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 178426949HCID 178426949, compound

Product 1

HCID 178426950HCID 178426950, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a dry 50 mL round bottomed flask, 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid (3-{3-[(4-hydroxymethyl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amide (as prepared in Example 331, 0.020 mg, 0.039 mmol) was dissolved in DMF (1 mL), under Ar(g). Dimethylaminoacetyl chloride hydrochloride (9.32 mg, 0.059 mmol) was then added followed by triethylamine (0.016 mL, 0.117 mmol). The mixture was stirred at room temperature for 2 hours after which the reaction mixture was partitioned between EtOAc (˜5 mL) and brine (˜5 mL). The organic layer was extracted with brine (3×5 mL). The organic layers were combined and then concentrated in vacuo. The crude residue was then chromatographed over silica (EtOAc/MeOH gradiant was used starting from 1% MeOH up to 5% MeOH). The pure product was isolated as a yellow solid (15.5 mg, 0.026 mmol, 67%).

Workup

  1. customwas partitioned between EtOAc (˜5 mL) and brine (˜5 mL)
  2. extractionThe organic layer was extracted with brine (3×5 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was then chromatographed over silica (EtOAc/MeOH gradiant

Sources & evidence

ORD record
ord-47870bb8e41a4f0e9f10be8166411f69
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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