Triethylamine → HCID 44242534, compound

HRID 1446066Notes

Reaction equation

HRID 1446066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:30]2[CH2:34][CH:33]([CH2:35][NH:36][C:37](=[O:39])[CH3:38])[O:32][C:31]2=[O:40])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][O:16][CH:17]2[CH2:22][O:21][C:20]3=[N:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][N:19]3[CH2:18]2)[CH2:10][CH2:9]1.[N+](C1N=C2N(C=1)CC(OCC(O)=O)CO2)([O-])=O.FC1C=C(N2CC(CNC(=O)C)OC2=O)C=CC=1N1CCNCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N:30]2[CH2:34][C@H:33]([CH2:35][NH:36][C:37](=[O:39])[CH3:38])[O:32][C:31]2=[O:40])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][O:16][C@@H:17]2[CH2:22][O:21][C:20]3=[N:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][N:19]3[CH2:18]2)[CH2:10][CH2:9]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18939356HCID 18939356, compoundHCID 68548045HCID 68548045, compoundHCID 68548178HCID 68548178, compound

Product 1

HCID 44242534HCID 44242534, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[3-(3-Fluoro-4-{4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-acetyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide. A mixture of (2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-acetic acid (53 mg, 0.22 mmol), N-[3-(3-fluoro-4-piperazin-1-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide (73 mg, 0.228 mmol) (prepared as described by Barbachyn et al, U.S. Pat. No. 5,547,950) and TBTU (114 mg, 0.35 mmol) is dissolved in DMF (5 ml) and treated with Et3N (0.122 ml, 0.88 mmol) and stirred at room temperature for 12 hours. The mixture was diluted with EtOAc and water. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was purified by preparative TLC to give 13 mg (10%) of the titled product as a tan solid. ESI MS m/z 562 (M+H+); 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=11.6 Hz, 1H), 7.44 (s, 1H), 7.21-7.02 (m, 1H), 7.00-6.85 (m, 1H), 5.99-5.92 (m, 1H), 4.76-4.67 (m, 2H), 4.44-4.22 (m, 4H), 4.05-4.01 (m, 1H), 3.79-3.44 (m, 4H), 3.49 (s, 2H), 3.10-2.62 (m, 4H), 2.02 (s, 3H), 1.24 (s, 3H).

Workup

  1. customprepared
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-6411674ff451413eb00c5f80d6987ab9
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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