Triethylamine → HCID 117610822, compound

HRID 588901Notes

Reaction equation

HRID 588901 reaction equation
[Br:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]([O:14][CH3:15])=[C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=O)[CH:7]=1.[N:17]1([CH:23]2[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24]2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C>[Br:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]([O:14][CH3:15])=[C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([N:20]2[CH2:21][CH2:22][N:17]([CH:23]3[CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26]3)[CH2:18][CH2:19]2)=[O:12])[CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19360775tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylateHCID 117610999HCID 117610999, compound

Product 1

HCID 117610822HCID 117610822, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-(5-bromo-4-chloro-2-methoxyphenylamino)propanoic acid (1.6 g, 5.21 mmol), tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate (1.88 g, 7.82 mmol), EDCI.HCl (2.0 g, 10.42 mmol), HOBt (1.41 g, 10.42 mmol) in DMF (20 mL) at 0° C., Et3N (1.58 g, 15.63 mmol) was added. The resulting mixture was stirred at RT for 16 h and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (methanol/dichloroethane=1:50) to afford the desired product (2.1 g, 76% yield). ESI-MS m/z: 531.3[M+H]+.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (methanol/dichloroethane=1:50)

Sources & evidence

ORD record
ord-1f1dfd48c1df453095da905570106e15
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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