2-(Trifluoromethyl)benzylamine → HCID 178482417, compound

HRID 1671763Notes

Reaction equation

HRID 1671763 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]=[C:5]([NH:15][C@@H:16]2[CH2:21][CH2:20][C@H:19]([C:22](O)=[O:23])[CH2:18][CH2:17]2)[N:4]=1.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]=[C:5]([NH:15][C@@H:16]2[CH2:17][CH2:18][C@H:19]([C:22]([NH:30][CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[C:26]([F:35])([F:36])[F:25])=[O:23])[CH2:20][CH2:21]2)[N:4]=1

Participants

6

Reactant 3

HCID 764472-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482422HCID 178482422, compound

Product 1

HCID 178482417HCID 178482417, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of cis-4-(4-(methylamino)-6-(piperidin-1-yl)-1,3,5-triazin-2-ylamino)cyclohexanecarboxylic acid (7.6 mg, 0.023 mmol, 1 equivalent), 2-trifluoromethyl benzylamine (4 μL, 0.03 mmol, 1.25 equivalents) and DMAP (0.6 mg, 0.2 equivalents) in dichloromethane (1.5 ml) was cooled with stirring in an ice bath. EDCl (6.6 mg, 0.034 mmol, 1.5 equivalents) was added. The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 2-3 hours. The solution was diluted with dichloromethane (1 ml), which was further washed with saturated sodium bicarbonate and water. The organic layer was dried and purified by HPLC (Luna 5μ C8(2), 100×21 mm, 28-70% CH3CN/H2O, 0.1% TFA, 20 min) to afford the final product (8.0 mg, yield 71%). MS (ES+): m/e 492.30 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 30 min and at room temperature for 2-3 hours
  2. washwas further washed with saturated sodium bicarbonate and water
  3. customThe organic layer was dried
  4. custompurified by HPLC (Luna 5μ C8(2), 100×21 mm, 28-70% CH3CN/H2O, 0.1% TFA, 20 min)

Sources & evidence

ORD record
ord-8f3c96cd591040ac9bf37d269a3585e0
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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