Trifluoroacetic acid → HCID 178482418, compound

HRID 1671771Notes

Reaction equation

HRID 1671771 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][C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23](O)=[O:24])[CH2:19][CH2:18]2)[N:4]=1.C(O)(C(F)(F)F)=O.[F:33][C:34]([F:44])([F:43])[C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38].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][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:6]=[C:5]([NH:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([NH:38][CH2:37][C:36]3[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=3[C:34]([F:33])([F:43])[F:44])=[O:24])[CH2:19][CH2:18]2)[N:4]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 764472-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482424HCID 178482424, compound

Product 1

HCID 178482418HCID 178482418, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of trans-4-(4-(methylamino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-ylamino)cyclohexanecarboxylic acid as TFA salt (18.4 mg, 0.04 mmol, 1 equivalent), 2-trifluoromethyl benzylamine (10.5 mg, 0.06 mmol, 1.5 equivalents) and DMAP (1.3 mg, 0.26 equivalents) in dichloromethane (1 ml) was cooled with stirring in an ice bath. EDCl (12.7 mg, 0.066 mmol, 1.65 equivalents) was added. The reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with dichloromethane (1 ml), which was further washed with saturated sodium bicarbonate and water. The solvent was removed to give the crude product, which was further purified by RP-HPLC (Luna 5μ, C8(2), 100×21 mm, 5-40% CH3CN/H2O, 0.1% TFA, 25 min) to give the final product (5.33 mg, 21.5%). MS (ES+): m/e 507.21 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. washwas further washed with saturated sodium bicarbonate and water
  3. customThe solvent was removed
  4. customto give the crude product, which
  5. customwas further purified by RP-HPLC (Luna 5μ, C8(2), 100×21 mm, 5-40% CH3CN/H2O, 0.1% TFA, 25 min)

Sources & evidence

ORD record
ord-0d57c64a67ea4fbdaedeb0f23db206d1
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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