Ethylmorpholine → HCID 69358672, compound

HRID 852670Notes

Reaction equation

HRID 852670 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([C:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])=[O:17])[CH:10]=[C:11]([CH:15]=1)[C:12](O)=[O:13].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.Cl.Cl.[NH2:57][C@@H:58]([CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C@H:59]([OH:73])[CH2:60][NH:61][C@@H:62]([CH3:72])[C:63]([NH:65][CH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][CH2:67]1)=[O:64]>CN(C=O)C>[CH2:74]([C@H:58]([NH:57][C:12](=[O:13])[C:11]1[CH:15]=[C:7]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[CH:8]=[C:9]([C:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])=[O:17])[CH:10]=1)[C@H:59]([OH:73])[CH2:60][NH:61][C@H:62]([C:63](=[O:64])[NH:65][CH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][CH2:67]1)[CH3:72])[C:75]1[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69356761HCID 69356761, compoundHCID 69359752HCID 69359752, compound

Product 1

HCID 69358672HCID 69358672, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-oxo-pyrrolidin-1-yl)-N,N-dipropyl-isophthalamic acid (A80) (66 mg, 0.2 mmol, 1 equiv) in DMF (5 ml) at room temperature was added EDAC.HCl (46 mg, 0.24 mmol, 1.2 equiv), HOBT (37 mg, 0.24 mmol, 1.2 equiv), 4-ethylmorpholine (153μ, 1.2 mmol, 6 equiv) and (S)-2-((2R,3S)-3-amino-2-hydroxy-4-phenyl-butylamino)-N-cyclohexyl-propionamide di-hydrochloride (C6) (82 mg, 0.2 mmol, 1 equiv). The resulting mixture was stirred for 3 h then concentrated in vacuo. The residue was diluted in CH2Cl2 and the organic phases washed with a saturated NaHCO3 aqueous solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by preparative LC/MS gave N-[(1S,2R)-1-benzyl-3-((S)-1-cyclohexylcarbamoylethylamino)-2-hydroxypropyl]-5-(2-oxopyrrolidin-1-yl)-N′,N′-dipropylisophthalamide (E1) (78 mg, 60%) as a white foam. [M+H]+=648.3 RT=2.70.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted in CH2Cl2
  3. washthe organic phases washed with a saturated NaHCO3 aqueous solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by preparative LC/MS

Sources & evidence

ORD record
ord-ad932a9f86f34f7cac11888c81f523b3
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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