Piperidine → HCID 66611240, compound

HRID 2204712Notes

Reaction equation

HRID 2204712 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:10]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[C:13]([CH:17]=2)[C:14](O)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[NH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.ON1C2N=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.O.C(Cl)CCl>[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[C:13]([C:14]([N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)=[O:15])[C:12]([C:18]([F:19])([F:20])[F:21])=[CH:11][C:10]=2[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66612055HCID 66612055, compound

Product 1

HCID 66611240HCID 66611240, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(phenylmethyl)oxy]-4-{[(phenylmethyl)oxy]carbonyl}-2-(trifluoromethyl)benzoic acid (may be prepared as described in Description 55; 142 mg, 0.14 mmol) in N,N-dimethylformamide (4 ml) was added diisopropylethylamine (120 ul), piperidine (0.05 ml, 0.52 mmol), 1-hydroxy-7-azabenzotriazole (60 mg), and EDC (120 mg). The solution was stirred for 18 hours. Water (10 ml) and ethyl acetate (10 ml) were added and the organic layer was separated, washed with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane) to yield the title compound as a gum. 170 mg.

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-c0ab7dca911746d587d730a1059aa8c0
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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