Diisopropylethylamine → 1-cyclopentyl-N-((1S,2R)-3-(((1R)-3,3-dimethyl-7-(methyloxy)-4-oxo-1,2,3,4-tetrahydro-1-naphthalenyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-6-oxo-5-(2-oxo-1-pyrrolidinyl)-1,6-dihydro-3-pyridinecarboxamide

HRID 253155Notes

Reaction equation

HRID 253155 reaction equation
[CH:1]1([N:6]2[C:11](=[O:12])[C:10](C3C=CC=CN=3)=[CH:9][C:8]([C:19]([OH:21])=O)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C([O:29]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:46][C@@H:47]([CH2:67][C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)[C@H:48]([OH:66])[CH2:49][NH:50][CH:51]1[C:60]2[C:55](=[CH:56][CH:57]=[C:58]([O:61][CH3:62])[CH:59]=2)[C:54](=[O:63])[C:53]([CH3:65])([CH3:64])[CH2:52]1.[CH:74]([N:77]([CH:80]([CH3:82])C)CC)([CH3:76])C>CN(C=O)C>[CH:1]1([N:6]2[C:11](=[O:12])[C:10]([N:77]3[CH2:74][CH2:76][CH2:82][C:80]3=[O:29])=[CH:9][C:8]([C:19]([NH:46][C@@H:47]([CH2:67][C:68]3[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=3)[C@H:48]([OH:66])[CH2:49][NH:50][C@H:51]3[C:60]4[C:55](=[CH:56][CH:57]=[C:58]([O:61][CH3:62])[CH:59]=4)[C:54](=[O:63])[C:53]([CH3:64])([CH3:65])[CH2:52]3)=[O:21])=[CH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]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 668448391-Cyclopentyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylic acidHCID 668448524-((2R,3S)-3-amino-2-hydroxy-4-phenylbutylamino)-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 668448901-cyclopentyl-N-((1S,2R)-3-(((1R)-3,3-dimethyl-7-(methyloxy)-4-oxo-1,2,3,4-tetrahydro-1-naphthalenyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-6-oxo-5-(2-oxo-1-pyrrolidinyl)-1,6-dihydro-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-cyclopentyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylic acid (0.0743 g, 0.261 mmol) was added to a vial followed by DMF (1 mL). HATU (0.15 g, 0.39 mmol) was added and the mixture was stirred for 5 minutes. 4-((2R,3S)-3-amino-2-hydroxy-4-phenylbutylamino)-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (0.100 g, 0.26 mmol) was added followed by the addition of diisopropylethylamine (0.18 ml, 1.0 mmol). Reaction was allowed to stir at RT. After 2 hours, reaction the crude reaction mixture was purified using the Gilson. The solvent was evaporated to provide the title compound as a white solid. MS m/z: 649.6 (M+1).

Workup

  1. customReaction
  2. stirringto stir at RT
  3. waitAfter 2 hours
  4. customreaction the crude
  5. customreaction mixture
  6. customwas purified
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1b128f0aa8224554bcefa7ea635952f9
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

Loading…