Diisopropylethylamine → Methyl (1-{3-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]-phenyl}acetyl)amino]propyl}cyclopropyl)acetate

HRID 238188Notes

Reaction equation

HRID 238188 reaction equation
[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1([CH2:38][CH2:39][CH2:40][NH2:41])[CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7]([NH:41][CH2:40][CH2:39][CH2:38][C:35]2([CH2:34][C:33]([O:32][CH3:31])=[O:42])[CH2:36][CH2:37]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

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 58074507cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acidHCID 131731181Methyl[1-(3-aminopropyl)cyclopropyl]acetate hydrochloride

Product 1

HCID 58074543Methyl (1-{3-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]-phenyl}acetyl)amino]propyl}cyclopropyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 591 mg (1.51 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxa-diazin-4-yl)methyl]phenyl}acetic acid (enantiomer 2), 376 mg (1.81 mmol) of methyl[1-(3-amino-propyl)cyclopropyl]acetate hydrochloride, 859 mg (2.26 mmol) of HATU and 1 ml of N,N-diiso-propylethylamine in 10 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the mixture was poured into ice-water, the phases were separated and the aqueous phase was extracted three times with tert-butyl methyl ether. The combined organic phases were dried over sodium sulfate, and, after filtration, the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by preparative RP-HPLC. This gave 233 mg (0.43 mmol, 28.5% of theory) of the title compound as a colorless oil.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted three times with tert-butyl methyl ether
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationafter filtration
  5. customthe solvent was removed to dryness under reduced pressure

Sources & evidence

ORD record
ord-306433ffada34b10b2a62c002c7d0136
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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