4-Methylbenzylamine → HCID 67142111, compound

HRID 1445097Notes

Reaction equation

HRID 1445097 reaction equation
[CH2:1]([N:4]1[C:8]2=[C:9]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[N:10]=[C:11]([C:13]([OH:15])=O)[CH:12]=[C:7]2[C:6]([CH3:26])=[C:5]1[CH3:27])[CH:2]=[CH2:3].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[CH3:60][C:61]1[CH:68]=[CH:67][C:64]([CH2:65][NH2:66])=[CH:63][CH:62]=1>ClCCl>[CH2:1]([N:4]1[C:8]2=[C:9]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[N:10]=[C:11]([C:13]([NH:66][CH2:65][C:64]3[CH:67]=[CH:68][C:61]([CH3:60])=[CH:62][CH:63]=3)=[O:15])[CH:12]=[C:7]2[C:6]([CH3:26])=[C:5]1[CH3:27])[CH:2]=[CH2:3]

Participants

7

Reactant 5

HCID 660354-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67141817HCID 67141817, compound

Product 1

HCID 67142111HCID 67142111, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-allyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carboxylic acid (30 mg, 0.083 mmol) prepared in Example 732, 1-hydroxybenzotriazole hydrate (16.9 mg, 0.125 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (23.9 mg, 0.125 mmol), diisopropylethylamine (43,4 μl, 0.25 mmol), and 4-methylbenzylamine (15.9 μl, 0.125 mmol) in dichloromethane (1 ml) was stirred for 2 hours at room temperature and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 9.1 mg of the titled compound as a white solid. (Yield: 45%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Sources & evidence

ORD record
ord-c871d3e089bd449f8ac891b7ae423ce6
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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