2,4-Dichlorobenzylamine → HCID 178482398, compound

HRID 1671758Notes

Reaction equation

HRID 1671758 reaction equation
[CH3:1][N:2]([C:12]1[N:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[N:13]=1)[C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1.[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[CH2:35][NH2:36].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.C(Cl)Cl.C(Cl)Cl>[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[CH2:35][NH:36][C:9]([C@H:6]1[CH2:7][CH2:8][C@@H:3]([N:2]([CH3:1])[C:12]2[N:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[N:13]=2)[CH2:4][CH2:5]1)=[O:10]

Participants

7

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482399HCID 178482399, compound

Product 1

HCID 178482398HCID 178482398, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of cis-4-{methyl[4-(methylamino)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxylic acid (50 mg, 0.138 mmol), [(2,4-dichlorophenyl)methyl]amine (30 mg, 0.17 mmol), and DMAP (3.37 mg, 0.028 mmol) in DMF/DCM was cooled in an ice bath. EDCl (40 mg, 0.21 mmol) was added. The reaction mixture was stirred at 0° C. for 0.5 hour, and then at room temperature for 2 hours. The solution was diluted with DCM and then washed with a saturated NaCl solution. The organic layer was dried over NaSO4 and concentrated to give the crude product which was purified by HPLC. After purification, 29 mg (0.06 mmol, 40% yield) of product was obtained as a white solid. MS (ES+): m/e 521.1 [M+H]+.

Workup

  1. waitat room temperature for 2 hours
  2. washwashed with a saturated NaCl solution
  3. dry with materialThe organic layer was dried over NaSO4
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by HPLC
  7. customAfter purification

Sources & evidence

ORD record
ord-a992bf8feeae4192a5d92d8f9ef8e095
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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