Morpholine → HCID 59625494, compound

HRID 2192820Notes

Reaction equation

HRID 2192820 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:43][CH:44]([CH3:46])[CH3:45])[C@H:21]2[CH2:26][C@@H:25]([NH:27][C:28](OCC(Cl)(Cl)Cl)=[O:29])[CH2:24][N:23]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[NH:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C)C(=O)C.Cl>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:43][CH:44]([CH3:46])[CH3:45])[C@H:21]2[CH2:26][C@@H:25]([NH:27][C:28]([N:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)=[O:29])[CH2:24][N:23]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59625246HCID 59625246, compound

Product 1

HCID 59625494HCID 59625494, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (3S,5R)-3-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-{[(2,2,2-trichloroethoxy)carbonyl]amino}piperidine-1-carboxylate (98.0 mg) and N,N-diisopropylethylamine (120 μl) were dissolved in N,N-dimethylacetamide (3 ml), morpholine (20 μl) was added, and the mixture was stirred at 80° C. for 1 day. The reaction mixture was diluted with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object compound (12.7 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe fraction eluted with ethyl acetate-hexane (10:90-100:0)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e4b529a1219f4e459687d8176693d771
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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