HCID 21874093, compound → HCID 10453531, compound

HRID 2213365Notes

Reaction equation

HRID 2213365 reaction equation
C1(C(C2C=CC=CC=2)CCO[C:11](=[S:15])[CH:12]([F:14])[F:13])C=CC=CC=1.[NH2:22][CH2:23][CH:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH:41]=[CH:40][C:39](=[O:42])[CH2:38][CH2:37]3)=[C:32]([F:43])[CH:31]=2)[CH2:25]1>CC#N.CN(C=O)C>[F:13][CH:12]([F:14])[C:11]([NH:22][CH2:23][CH:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH:37]=[CH:38][C:39](=[O:42])[CH2:40][CH2:41]3)=[C:32]([F:43])[CH:31]=2)[CH2:25]1)=[S:15]

Participants

5

Reactant 2

HCID 21874093HCID 21874093, compoundHCID 21957319HCID 21957319, compound

Product 1

HCID 10453531HCID 10453531, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Difluoro-thioacetic acid-O-(3,3-diphenyl-propyl)ester (84 mg, 0.25 mmol) is added to a solution of 1-[4-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,3-dihydro-1H-pyridin-4-one in MeCN (1.2 mL) and DMF (0.2 mL). This solution is stirred for 36 h at which time the reaction is concentrated under reduced pressure and the title compound is purified by silica gel column chromatography (eluent: 1% MeOH in EtOAc). Yield 45 mg (41%). MS (m/z) 400 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ 11.32 (s, 1H), 7.83–7.51 (m, 4H), 6.69 (t, J=55.2 Hz, 1H), 5.25–5.17 (m, 2H), 4.39 (t, J=9.1 Hz,1H), 4.22–4.03 (m, 6H), 3.55–3.49 (m, 2H).

Workup

  1. concentrationis concentrated under reduced pressure
  2. customthe title compound is purified by silica gel column chromatography (eluent: 1% MeOH in EtOAc)

Sources & evidence

ORD record
ord-78a9ff1d1f344b5f8fa3f96c6d492756
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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