Diisopropylethylamine → HCID 67065485, compound

HRID 1967112Notes

Reaction equation

HRID 1967112 reaction equation
[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.[NH2:10][C@@H:11]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([F:34])([F:33])[F:32])[CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([NH:10][C@@H:11]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:32])[F:33])[CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 133335605-Bromofuran-3-carboxylic acidHCID 578268082-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67065485HCID 67065485, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3-furancarboxylic acid (0.30 g, 1.57 mmol) [prepared according to J. Org. Chem. 1976, 41, 2350.], 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione (0.60 g, 1.73 mmol) [from Preparation 5] and diisopropylethyl amine (0.82 mL, 4.7 mmol) in DCM (50 mL) at 25° C. was added PyBrOP (1.09 g, 2.36 mmol) in one portion. After 16 h, the solution was partitioned between H2O and washed with DCM. The combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica, hexanes/EtOAc, 1:1) affording the title compound (0.45 g, 55%) as a white solid: LC-MS (ES) m/z=521 (WH)+.

Workup

  1. customthe solution was partitioned between H2O
  2. washwashed with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-9902db18f1324f1ea1f36c32d934ce1b
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

Loading…