Water → HCID 86704630, compound

HRID 1508582Notes

Reaction equation

HRID 1508582 reaction equation
FC(F)(F)C([O-])=O.[N:8]1([C:12]2[NH+:17]=[C:16]([CH2:18][N:19]3[C@@H:23]([CH3:24])[C@@H:22]([C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=4)[O:21][C:20]3=[O:39])[C:15]([C:40]3[CH:45]=[C:44]([CH2:46][C:47]#[N:48])[CH:43]=[CH:42][C:41]=3[O:49][CH3:50])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1.Cl.C(N(CC)CC)C.[N-:59]=[N+:60]=[N-:61].[Na+].O>CN1C(=O)CCC1>[N:8]1([C:12]2[N:17]=[C:16]([CH2:18][N:19]3[C@@H:23]([CH3:24])[C@@H:22]([C:25]4[CH:26]=[C:27]([C:35]([F:36])([F:37])[F:38])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=4)[O:21][C:20]3=[O:39])[C:15]([C:40]3[CH:45]=[C:44]([CH2:46][C:47]4[N:59]=[N:60][NH:61][N:48]=4)[CH:43]=[CH:42][C:41]=3[O:49][CH3:50])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 86704631HCID 86704631, compound

Product 1

HCID 86704630HCID 86704630, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-3-[5-(cyanomethyl)-2-methoxyphenyl]pyridinium trifluoroacetate (EXAMPLE 256) (15 mg, 0.021 mmol), triethylamine hydrochloride (15 mg, 0.109 mmol), and sodium azide (30 mg, 0.461 mmol) in NMP (2 ml) was stirred at 150° C. under nitrogen for 3 days. Water was added and the mixture extracted 2 times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by RP HPLC to afford the title compound. Mass spectrum (ESI) 648.3 (M+1). 1H NMR (500 MHz, CD3OD): δ 7.97 (s, 1H); 7.88 (s, 2H); 7.30 (d, J=8.4 Hz, 1H); 7.26 (m, 1H); 7.08 (s, 1H); 7.01 (d, J=8.5 Hz, 1H); 6.34 (d, J=8.4 Hz, 1H); 5.70 (m, 1H); 4.62 (d, J=14.3 Hz, 1H); 4.25 (s, 2H); 4.20 (s, 1H); 4.04 (t, J=7.4 Hz, 4H); 3.86 (br s, 1H); 3.77 (s, 3H); 2.43-2.36 (m, 2H); 0.59 (m, 3H).

Workup

  1. extractionthe mixture extracted 2 times with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by RP HPLC

Sources & evidence

ORD record
ord-545e03d5f9324c589e7aef744d580a84
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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