Triethylamine → HCID 56969408, compound

HRID 1508569Notes

Reaction equation

HRID 1508569 reaction equation
Cl.[CH3:2][O:3][CH:4]1[CH2:7][NH:6][CH2:5]1.[F:8][C:9]([F:53])([F:52])[C:10]1[CH:11]=[C:12]([C@H:20]2[O:24][C:23](=[O:25])[N:22]([CH2:26][C:27]3[C:32]([C:33]4[CH:34]=[C:35]([CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:36]=[CH:37][C:38]=4[O:39][CH3:40])=[CH:31][N:30]=[C:29](S(C)(=O)=O)[N:28]=3)[C@H:21]2[CH3:51])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.C(N(CC)CC)C>C1COCC1>[F:53][C:9]([F:8])([F:52])[C:10]1[CH:11]=[C:12]([C@H:20]2[O:24][C:23](=[O:25])[N:22]([CH2:26][C:27]3[C:32]([C:33]4[CH:34]=[C:35]([CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:36]=[CH:37][C:38]=4[O:39][CH3:40])=[CH:31][N:30]=[C:29]([N:6]4[CH2:7][CH:4]([O:3][CH3:2])[CH2:5]4)[N:28]=3)[C@H:21]2[CH3:51])[CH:13]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 222428583-Methoxyazetidine hydrochlorideHCID 86704618HCID 86704618, compound

Product 1

HCID 56969408HCID 56969408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxy-azetidine hydrochloride (60.4 mg, 0.488 mmol) was added into a stirred mixture of methyl 3-{3-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-4-methoxyphenyl}propanoate (66 mg, 0.098 mmol) and triethylamine (0.068 mL, 0.488 mmol) in THF (1 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The yellow reaction crude was concentrated in vacuo. The resulting pot residue was purified by preparative HPLC (reverse phase, SunFire Prep C18 OBD 5 um 19×150 mm) eluting with acetonitrile/water+0.05% HCOOH (20% to 100% organic in 10 min, hold 100% for 2 min, 20 mL/min) to give a colorless glass as the titled compound. LCMS calc.=682.22. found=683.27 (M+H)+. 1H-NMR (CDCl3, 500 MHz) δ 8.12 (s, 1H), 7.86 (s, 1H), 7.73 (s, 2H), 7.20 (dd, J=8.5, 2.0 Hz, 1H), 6.97 (d, J=1.5 Hz, 1H), 6.88 (d, J=8.5 Hz, 1H), 5.59 (br d, J=8.0 Hz, 1H), 4.73 (br d, J=17 Hz, 1H), 4.41-4.32 (m, 3H), 4.28 (br s, 1H), 4.11-4.03 (m, 2H), 3.91 (br s, 1H), 3.77 (s, 3H), 3.64 (s, 3H), 3.37 (s, 3H), 2.92 (t, J=7.5 Hz, 2H), 2.62 (t, J=7.5 Hz, 2H), 0.66 (br s, 3H).

Workup

  1. customThe yellow reaction crude
  2. concentrationwas concentrated in vacuo
  3. customThe resulting pot residue was purified by preparative HPLC (reverse phase, SunFire Prep C18 OBD 5 um 19×150 mm)
  4. washeluting with acetonitrile/water+0.05% HCOOH (20% to 100% organic in 10 min, hold 100% for 2 min, 20 mL/min)

Sources & evidence

ORD record
ord-4948846c7ae04c3f8bcd35fa2b3a3f7b
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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