N,N-Dimethylethylenediamine → 2-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-N-(2-(dimethylamino)ethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxamide

HRID 907279Notes

Reaction equation

HRID 907279 reaction equation
[CH2:1]([N:8]1[CH:17]=[C:16]([C:18]([OH:20])=O)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:21]3[CH:26]=[C:25]([C:27](=[O:32])[NH:28][CH:29]4[CH2:31][CH2:30]4)[CH:24]=[CH:23][C:22]=3[CH3:33])[CH:14]=2)[C:9]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38][NH2:39].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[CH2:1]([N:8]1[CH:17]=[C:16]([C:18]([NH:39][CH2:38][CH2:37][N:36]([CH3:40])[CH3:35])=[O:20])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:21]3[CH:26]=[C:25]([C:27](=[O:32])[NH:28][CH:29]4[CH2:31][CH2:30]4)[CH:24]=[CH:23][C:22]=3[CH3:33])[CH:14]=2)[C:9]1=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575517272-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

Product 1

HCID 250205142-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-N-(2-(dimethylamino)ethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the product of step iii) (0.48 g) and N,N-dimethylethane-1,2-diamine (0.17 mL) in THF (20 mL) was added N,N-diisopropylethylamine (0.56 mL) followed by HATU (0.60 g) and the reaction stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness and the crude product purified by SiO2 chromatography (eluting with 90:10:0.1 dichloromethane:methanol:triethylamine). The fractions containing product were concentrated to dryness and the residue triturated with acetonitrile to give the title compound as a solid (0.35 g).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe crude product purified by SiO2 chromatography (eluting with 90:10:0.1 dichloromethane:methanol:triethylamine)
  3. additionThe fractions containing product
  4. concentrationwere concentrated to dryness
  5. customthe residue triturated with acetonitrile

Sources & evidence

ORD record
ord-ce728a75336842deae0190c595b171a8
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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