1,2-Dichloroethane → HCID 59640438, compound

HRID 2250144Notes

Reaction equation

HRID 2250144 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:6]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69313847HCID 69313847, compound

Product 1

HCID 59640438HCID 59640438, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-Fluoro-4-(3-piperidin-1-yl-propoxy)-benzoic acid (70 mg, 0.25 mmol) and 1-(2-aminoethyl)piperidine (450 □L, 0.3 mmol) in DMF (5 mL) was added EDC (58 mg, 0.3 mmol), HOBT (40 mg, 0.3 mmol), and diisopropylethyl amine (52 □1, 0.3 mmol). The mixture was stirred at room temperature overnight. The mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (Biotage 12 M, elute 90/10/1 CH2Cl2/MeOH/NH4OH) to yield the title compound. MS (ES+) 392.3

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (Biotage 12 M, elute 90/10/1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-0df390e4d9e84c99a1a1636f443af896
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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