4-Methylmorpholine → HCID 86722690, compound

HRID 1480466Notes

Reaction equation

HRID 1480466 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[O:19][CH2:20][C:21](O)=[O:22].CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(Cl)Cl>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:21](=[O:22])[CH2:20][O:19][C:18]2[CH:17]=[C:16]([Cl:15])[CH:26]=[C:25]([Cl:27])[CH:24]=2)[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 11484(3,5-Dichlorophenoxy)acetic acidHCID 7238334-(N-Boc-amino)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86722690HCID 86722690, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl piperidin-4-ylcarbamate (300 mg, 1.498 mmol) and 2-(3,5-dichlorophenoxy)acetic acid 331 mg, 1.498 mmol) in DMF (5 mL) at RT was added NMM (0.329 mL, 3.00 mmol) and EDC.HCl (287 mg, 1.498 mmol). The reaction mixture was stirred for 5 hours, diluted with DCM and washed with a saturated solution of sodium bicarbonate, brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-50% EtOAc in hexanes to afford the title product.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-ee8d2aec51f7492fab4c00c1e3c734bf
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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