1,2-Dichloroethane → HCID 66998209, compound

HRID 537413Notes

Reaction equation

HRID 537413 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]1)=[O:22])[CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[NH3:34]>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:21]([N:23]1[CH2:24][CH2:25][CH:26]([CH3:29])[CH2:27][CH2:28]1)=[O:22])[CH2:10][CH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:14]([C:15](=[O:16])[NH2:34])[CH:13]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 66997971HCID 66997971, compound

Product 1

HCID 66998209HCID 66998209, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 85 mg (0.21 mmol) of 3-[3-tert-butoxycarbonylamino-4-(4-methyl-piperidin-1-yl)-4-oxo-butyl]-benzoic acid, 81 mg (0.42 mmol) of EDC, 57 mg (0.42 mmol), and 2.6 mg (0.021 mmol) of DMAP is stirred in DMF for 2 h at rt. After cooling to −40° C. ˜0.2 mL of NH3 is condensed into the mixture. The resulting solution is sealed and stirred at rt for 10 h. The mixture is concentrated and purified by preparatory TLC (10% MeOH in CH2Cl2) to provide 66 mg (78%) of [3-(3-carbamoyl-phenyl)-1-(4-methyl-piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester.

Workup

  1. customcondensed into the mixture
  2. customThe resulting solution is sealed
  3. concentrationThe mixture is concentrated
  4. custompurified by preparatory TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9aa0ccc89c2b4553a63723e2b2501bbd
Source dataset
uspto-grants-2014_10
Patent number
US08859814B2

Reaction notes

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