Azetidine → HCID 86704649, compound

HRID 1508602Notes

Reaction equation

HRID 1508602 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[C:21]([C:22]4[CH:23]=[C:24]([C:30]5[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][C:31]=5[CH3:40])[CH:25]=[CH:26][C:27]=4[O:28][CH3:29])=[CH:20][N:19]=[C:18](S(C)(=O)=O)[N:17]=3)[C@H:10]2[CH3:45])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:46]1[CH2:49][CH2:48][CH2:47]1>C1COCC1>[N:46]1([C:18]2[N:17]=[C:16]([CH2:15][N:11]3[C@@H:10]([CH3:45])[C@@H:9]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=4)[O:13][C:12]3=[O:14])[C:21]([C:22]3[CH:23]=[C:24]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][C:31]=4[CH3:40])[CH:25]=[CH:26][C:27]=3[O:28][CH3:29])=[CH:20][N:19]=2)[CH2:49][CH2:48][CH2:47]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 86704650HCID 86704650, compound

Product 1

HCID 86704649HCID 86704649, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3′-[4-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-2-(methylsulfonyl)pyrimidin-5-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate (81 mg, 0.121 mmol) in THF (1.6 mL) was added azetidine (40.7 μL, 0.604 mmol). The reaction was subjected to microwave irradiation at 100° C. for 15 min. The reaction was concentrated, then dissolved in ethyl acetate and washed with water (2×), brine, dried (Na2SO4), filtered, concentrated. The crude reaction was purified by column chromatography to yield methyl 3′-[2-(azetidin-1-yl)-4-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}pyrimidin-5-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate (78 mg, 0.121 mmol). LCMS calc.=647.2. found=647.4.

Workup

  1. customirradiation at 100° C. for 15 min
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water (2×), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude reaction
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-96f34e0c9d8d4d8c95910e5d32768423
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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