Ethylenediamine → HCID 86681282, compound

HRID 1467337Notes

Reaction equation

HRID 1467337 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[F:5][C:6]1[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[C:7]=1[CH2:8][N:9]1[CH2:14][C@H:13]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][N:22]=[C:21]3[C:27]2[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=2)=[O:17])[CH2:12][CH2:11][C@H:10]1[C:34](O)=[O:35].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>CN(C)C=O>[NH2:3][CH2:2][CH2:1][NH:4][C:34]([C@H:10]1[N:9]([CH2:8][C:7]2[C:37]([O:41][CH3:42])=[CH:38][CH:39]=[CH:40][C:6]=2[F:5])[CH2:14][C@H:13]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][N:22]=[C:21]3[C:27]2[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=2)=[O:17])[CH2:12][CH2:11]1)=[O:35]

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67996739HCID 67996739, compound

Product 1

HCID 86681282HCID 86681282, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

ethane-1,2-diamine (18 mg, 0.290 mmol) was added to a stirred mixture of (2S,5R)-1-(2-fluoro-6-methoxybenzyl)-5-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)-piperidine-2-carboxylic acid (50 mg, 0.097 mmol), N,N-DIISOPROPYLETHYL-AMINE (0.084 ml, 0.483 mmol), HATU (73.5 mg, 0.193 mmol) in dimethylformamide and the mixture was stirred at room temperature for Overnight. The reaction was rotovap to dryness and the residue was purified by column chromatography on silica gel Isolute Flash Si; 50 g prepacked, eluting with 5% MeOH/NH3(2M)CH2Cl2 to give the desired (48.1 mg, 0.085 mmol, 88% yield) as a white solid.

Workup

  1. customthe residue was purified by column chromatography on silica gel Isolute Flash Si
  2. washeluting with 5% MeOH/NH3(2M)CH2Cl2
  3. customto give the

Sources & evidence

ORD record
ord-23122541c5c04f2285988fcdfaa2024a
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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