Diisopropylethylamine → 4-{[6-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-1-oxo-2-pyridin-4-ylmethyl-1,2-dihydro-isoquinoline-4-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 907284Notes

Reaction equation

HRID 907284 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.[NH2:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]1.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>O1CCCC1>[C:45]([O:44][C:42]([N:39]1[CH2:40][CH2:41][CH:36]([NH:35][C:31]([C:16]2[C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:11]4[CH:12]=[C:7]([C:5](=[O:6])[NH:4][CH:1]5[CH2:2][CH2:3]5)[CH:8]=[CH:9][C:10]=4[CH3:34])[CH:14]=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]=2)=[O:32])[CH2:37][CH2:38]1)=[O:43])([CH3:48])([CH3:46])[CH3:47]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 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 575517434-{[6-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-1-oxo-2-pyridin-4-ylmethyl-1,2-dihydro-isoquinoline-4-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the product of Example 54 step iii) (0.1 g), 4-amino-N-boc-piperadine (0.05 g) and N,N-diisopropylethylamine (0.25 mL) in tetrahydrofuran (10 mL) was added HATU (0.16 g) and the mixture stirred at room temperature for 3 hours. The reaction mixture was then concentrated to dryness and the crude product purified HPLC to give the sub-title compound (0.09 g).

Workup

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

Sources & evidence

ORD record
ord-eca3dc0f49e34e8aad99160461302987
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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