Sodium Iodide → HCID 178473293, compound

HRID 506367Notes

Reaction equation

HRID 506367 reaction equation
C[Si](Cl)(C)C.[CH2:6]([O:8][C:9]([N:11]1[C:20]2[C:15](=[N:16][C:17]([O:21]C)=[CH:18][CH:19]=2)[C@@H:14]([NH:23][C:24]2[N:29]=[C:28]([CH2:30][C:31]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=3)[C:27]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)=[CH:26][N:25]=2)[CH2:13][C@H:12]1[CH2:51][CH3:52])=[O:10])[CH3:7].[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.C(#N)C>[CH2:6]([O:8][C:9]([N:11]1[C:20]2[C:15](=[N:16][C:17]([OH:21])=[CH:18][CH:19]=2)[C@@H:14]([NH:23][C:24]2[N:29]=[C:28]([CH2:30][C:31]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:42])[F:43])[CH:32]=3)[C:27]([N:45]3[CH2:46][CH2:47][O:48][CH2:49][CH2:50]3)=[CH:26][N:25]=2)[CH2:13][C@H:12]1[CH2:51][CH3:52])=[O:10])[CH3:7]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 16725542HCID 16725542, compound

Product 1

HCID 178473293HCID 178473293, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trimethylsilyl chloride (4.6 ml) is added dropwise to a suspension of (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(morpholin-4-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (2.4 g), sodium iodide (5.4 g) and acetonitrile (50 ml) at 80° C. After addition, the reaction solution is cooled to room temperature, and a saturated aqueous sodium thiosulfate solution and ethyl acetate are added thereto. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane: ethyl acetate=2:1→0:1) to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(morpholin-4-yl)pyrimidin-2-yl]}amino-2-ethyl-6-hydroxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (988 mg). MS (m/z): 655 [M+H]+

Workup

  1. additionAfter addition
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by column chromatography (silica gel; hexane: ethyl acetate=2:1→0:1)

Sources & evidence

ORD record
ord-2eca5721cb1849d7a9119c3ede8ce929
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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