Diisopropylethylamine → tert-Butyl(+/-)-1-{3-[(cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-methyl]phenyl}acetyl)amino]benzyl}cyclopropanecarboxylate

HRID 877256Notes

Reaction equation

HRID 877256 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.[CH:19]1([CH:24]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:35]3[CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[CH:40][C:41]=4[F:44])[C:36]3=[O:45])=[CH:30][CH:29]=2)[C:25](O)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:19]1([CH:24]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:35]3[CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[CH:40][C:41]=4[F:44])[C:36]3=[O:45])=[CH:30][CH:29]=2)[C:25]([NH:1][C:2]2[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=2)[CH2:5][C:6]2([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:8][CH2:7]2)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58136462cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetic acidHCID 58136514tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate

Product 1

HCID 58136491tert-Butyl(+/-)-1-{3-[(cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-methyl]phenyl}acetyl)amino]benzyl}cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

77.5 mg (0.31 mmol) of tert-butyl 1-(3-aminobenzyl)cyclopropanecarboxylate were added to a solution of 96 mg (0.26 mmol) of cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetic acid in 1 ml of DMF. At 0° C., 136 μl (0.78 mmol) of DIEA and then, a little at a time, 119.2 mg (0.31 mmol) of HATU were added to the resulting mixture. The reaction mixture was then slowly warmed to RT and stirred at RT for 1 h. The reaction mixture was added to water and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. This gave 146 mg (93% of theory) of the title compound.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84270f002e0143b5b68af2d509ca8cf1
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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