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)-2'-oxo-1',2'-dihydro-2,3'-bipyridine-5'-carboxamide

HRID 253154Notes

Reaction equation

HRID 253154 reaction equation
[CH:1]1([N:6]2[C:11](=[O:12])[C:10](N3CCCC3=O)=[CH:9][C:8]([C:19]([OH:21])=O)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=N[C:32]2[CH:33]=[CH:34][CH:35]=[N:36][C:31]1=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.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:1]1([N:6]2[CH:7]=[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:9]=[C:10]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:36]=3)[C:11]2=[O:12])[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 668447551-Cyclopentyl-6-oxo-5-(2-oxopyrrolidin-1-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 668447501'-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)-2'-oxo-1',2'-dihydro-2,3'-bipyridine-5'-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Cyclopentyl-6-oxo-5-(2-oxopyrrolidin-1-yl)-1,6-dihydropyridine-3-carboxylic acid (0.076 g, 0.26 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: 655.6 (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-db1e2019d84c4bcb9b5af2ffcaa4d219
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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