Diisopropylethylamine → N-Cyclopropyl-4-methyl-3-(1-oxo-2-(pyridin-4-ylmethyl)-4-(4-(pyrrolidin-1-yl)piperidine-1-carbonyl)-1,2-dihydroisoquinolin-6-yl)benzamide

HRID 907283Notes

Reaction equation

HRID 907283 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:34])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH:17]=[C:16]4[C:31](O)=[O:32])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[CH:35]([N:38]([CH2:42][CH3:43])[CH:39]([CH3:41])[CH3:40])([CH3:37])C.[CH3:44][N:45](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:46].F[P-](F)(F)(F)(F)F>O1CCCC1>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:34])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH:17]=[C:16]4[C:31]([N:45]3[CH2:46][CH2:40][CH:39]([N:38]4[CH2:35][CH2:37][CH2:43][CH2:42]4)[CH2:41][CH2:44]3)=[O:32])[CH:12]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575517776-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-2-(pyridin-4-ylmethyl)-1,2-dihydroisoquinoline-4-carboxylic acid

Product 1

HCID 25020619N-Cyclopropyl-4-methyl-3-(1-oxo-2-(pyridin-4-ylmethyl)-4-(4-(pyrrolidin-1-yl)piperidine-1-carbonyl)-1,2-dihydroisoquinolin-6-yl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the product of step iii) (0.1 g), 4-(N-pyrrolidin-1-yl)piperidine (0.037 g) and N,N-diisopropylethylamine (0.25 mL) in tetrahydrofuran (10 mL) was added HATU (0.17 g) and then stirred at room temperature for 3 hours. The reaction mixture was then concentrated to dryness and the crude product purified by HPLC to afford the title compound as a solid (0.07 g).

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. customthe crude product purified by HPLC

Sources & evidence

ORD record
ord-6d9d28530909445abbd5a303e69cf1ee
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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