Diisopropylethylamine → HCID 59354995, compound

HRID 2196424Notes

Reaction equation

HRID 2196424 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=O.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:50][C@@H:51]([CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=1[C:71]([F:74])([F:73])[F:72])[CH2:52][N:53]1[C:61](=[O:62])[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:54]1=[O:63]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1)[C:5]([NH:50][C@@H:51]([CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=1[C:71]([F:74])([F:72])[F:73])[CH2:52][N:53]1[C:61](=[O:62])[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:54]1=[O:63])=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 578268082-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dioneHCID 59355029HCID 59355029, compound

Product 1

HCID 59354995HCID 59354995, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-(1-methyl-1H-pyrazol-5-yl)benzoic acid (100 mg, 0.36 mmol), PyBrOP (277 mg, 0.59 mmol) and diisopropylethyl amine (0.11 mL, 0.59 mmol) in DCM (6 mL) at 25° C. was added 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione (161 mg, 0.36 mmol) [prepared according to Preparation 3]. After 16 h, the solution was concentrated and purified via column chromatography (silica, hexanes/EtOAc, 2:1) affording the title compound (172 mg, 78%) as a white solid: LC-MS (ES) m/z=612 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. custompurified via column chromatography (silica, hexanes/EtOAc, 2:1)

Sources & evidence

ORD record
ord-123c064772914c40b65d7c0c1b63a6da
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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