4-Methylmorpholine → HCID 71008704, compound

HRID 1845970Notes

Reaction equation

HRID 1845970 reaction equation
Cl.[NH2:2][C@@H:3]1[C:17](=[O:18])[N:16]2[CH2:19][C@H:20]([O:22][C:23]3[N:24]=[C:25]4[C:30](=[C:31]5[C:36]=3[CH:35]=[CH:34][CH:33]=[CH:32]5)[CH:29]=[CH:28][C:27]([F:37])=[CH:26]4)[CH2:21][C@H:15]2[C:14](=[O:38])[NH:13][C@:12]2([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:39][C@H:11]2[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CN1CCOCC1.[CH3:52][C:53]1[O:57][N:56]=[C:55]([C:58](O)=[O:59])[CH:54]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.Cl>[F:37][C:27]1[CH:28]=[CH:29][C:30]2[C:25]([CH:26]=1)=[N:24][C:23]([O:22][C@H:20]1[CH2:19][N:16]3[C:17](=[O:18])[C@@H:3]([NH:2][C:58]([C:55]4[CH:54]=[C:53]([CH3:52])[O:57][N:56]=4)=[O:59])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][C@@H:11]4[CH2:39][C@@:12]4([C:40]([O:42][CH2:43][CH3:44])=[O:41])[NH:13][C:14](=[O:38])[C@@H:15]3[CH2:21]1)=[C:36]1[C:31]=2[CH:32]=[CH:33][CH:34]=[CH:35]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71008839HCID 71008839, compound

Product 1

HCID 71008704HCID 71008704, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-amino-2-(3-fluorophenanthridin-6-yloxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 1d, 1.11 g, 1.89 mmol) was dissolved in dimethylformamide (19 mL) and treated with N-methylmorpholine (0.73 ml, 6.6 mmol) followed by 5-methylisoxazole-3-carboxylic acid (0.264 g, 2.074 mmol) and HATU (0.860 g, 2.263 mmol). The reaction mixture was stirred at room temperature for 1 h, diluted with 2 N HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with acetone/hexane, to provide the title compound (0.94 g, 72% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with acetone/hexane

Sources & evidence

ORD record
ord-bcf687bbc845420ea0bce0f767511a0b
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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