Diisopropylethylamine → HCID 90455837, compound

HRID 588865Notes

Reaction equation

HRID 588865 reaction equation
[Br:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:7]=1.[N:16]1([CH:22]2[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:29]([O:28][C:26]([N:24]1[CH2:25][CH:22]([N:16]2[CH2:21][CH2:20][N:19]([C:10](=[O:12])[CH2:9][CH2:8][C:6]3[CH:7]=[C:2]([Br:1])[C:3]([Cl:15])=[CH:4][C:5]=3[O:13][CH3:14])[CH2:18][CH2:17]2)[CH2:23]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19360775tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylateHCID 117607186HCID 117607186, compound

Product 1

HCID 90455837HCID 90455837, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-(5-bromo-4-chloro-2-methoxyphenyl)propanoic acid (350 mg, 1.2 mmol) in DMF (30 mL) at RT, tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate (317 mg, 1.3 mmol), BOP (731 mg, 1.4 mmol) and DIEA (461 mg, 3.6 mmol) were added and the mixture was stirred at RT for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the desired product (285 mg, 46% yield).

Workup

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

Sources & evidence

ORD record
ord-044f03d3032f4407b6ce681fe261a558
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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