4-Methylmorpholine → 6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N-(2-oxopropyl)pyridazine-3-carboxamide

HRID 46200Notes

Reaction equation

HRID 46200 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25]C3C=CC=CC=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11](O)=[O:12])=[CH:7][CH:6]=1.F[C:58](F)(F)[C:59]([OH:61])=O.[NH2:64][CH2:65]C(=O)C.CCN=C=NCCCN(C)C.O.ON1[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][C:85]=2N=N1.CN1CCOCC1>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25][C:85]3[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11]([NH:64][CH2:65][C:59](=[O:61])[CH3:58])=[O:12])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672878076-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acidHCID 86664428HCID 86664428, compound

Product 1

HCID 672883166-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N-(2-oxopropyl)pyridazine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid (1.2 mmol), 1-aminopropan-2-one trifluoroacetic acid salt (346 mg, 1.9 mmol), EDCI (472 mg, 2.5 mmol), and 1-hydroxybenzotriazole hydrate (478 mg, 3.1 mmol) in N,N-dimethylformamide (10 mL) was added 4-methylmorpholine (0.68 mL, 6.2 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine prior to drying over magnesium sulfate. Filtration through a plug of silica gel and removal of the volatiles under reduced pressure yielded titled compound as a brown amorphous solid, which was used without further purification.

Workup

  1. washAfter dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration
  4. customthrough a plug of silica gel and removal of the volatiles under reduced pressure

Sources & evidence

ORD record
ord-1212c87af3bb44879fb9252dec74a92d
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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