2,4-Dichlorobenzylamine → HCID 178482420, compound

HRID 1671754Notes

Reaction equation

HRID 1671754 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:6]=[C:5]([NH:16][CH:17]2[CH2:22][CH2:21][CH:20]([C:23](O)=[O:24])[CH2:19][CH2:18]2)[N:4]=1.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[CH2:34][NH2:35].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[CH2:34][NH:35][C:23]([C@H:20]1[CH2:21][CH2:22][C@@H:17]([NH:16][C:5]2[N:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[N:6]=2)[CH2:18][CH2:19]1)=[O:24]

Participants

6

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67330775trans-4-(4-(Methylamino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-ylamino)cyclohexanecarboxylic acid

Product 1

HCID 178482420HCID 178482420, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-{[4-(methylamino)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxylic acid (150 mg, 0.43 mmol), [(2,4-dichlorophenyl)methyl]amine (95 mg, 0.54 mmol) and DMAP (8 mg, 0.06 mmol) in DCM was stirred at room temperature. To this was added EDCl (90.8 mg, 0.47 mmol) and the resulting mixture was allowed to stir overnight. The solution was washed with water. The organic layer was dried and purified by HPLC to afford 78 mg (36% yield) of the product as a white solid. MS (ES+): m/e 507.1 [M+H]+.

Workup

  1. washThe solution was washed with water
  2. customThe organic layer was dried
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-622b5f6e63e14e6b9556f77da12b8295
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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