2,4-Dichlorobenzylamine → HCID 59028040, compound

HRID 251859Notes

Reaction equation

HRID 251859 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].C(N(C(C)C)CC)(C)C.[F:20][C:21]1[CH:22]=[C:23]2[C:28](=[C:29]([O:43][CH3:44])[C:30]=1[N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:33][CH2:32]1)[N:27]([C@@H:45]1[CH2:47][C@@H:46]1[F:48])[CH:26]=[C:25]([C:49](O)=[O:50])[C:24]2=[O:52]>CN(C)C=O.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:49]([C:25]1[C:24](=[O:52])[C:23]2[C:28](=[C:29]([O:43][CH3:44])[C:30]([N:31]3[CH2:32][CH2:33][N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:35][CH2:36]3)=[C:21]([F:20])[CH:22]=2)[N:27]([C@@H:45]2[CH2:47][C@@H:46]2[F:48])[CH:26]=1)=[O:50]

Participants

6

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 81531DiisopropylethylamineHCID 59027983HCID 59027983, compound

Product 1

HCID 59028040HCID 59028040, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

140 mg (0.27 mmol) of 1-benzotriazolyloxytripyrrolidinophosphonium hexafluorophosphate, 47 mg (0.27 mmol) of 2,4-dichlorobenzylamine and 35 mg (0.27 mmol) of diisopropylethylamine are added under argon to 105 mg (0.14 mmol) of the carboxylic acid of Example 6A in 2 ml of dimethylformamide and the mixture is stirred at room temperature for 2 days. The reaction mixture is diluted with 2 ml of water and without further work-up purified by preparative HPLC (Method 4). 52 mg of the target compound are obtained.

Workup

  1. custompurified by preparative HPLC (Method 4)

Sources & evidence

ORD record
ord-92c57e1619a648c7b18f9984f37cb45c
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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