1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44242067, compound

HRID 1446055Notes

Reaction equation

HRID 1446055 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:38]2[CH2:42][C@H:41]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:40][C:39]2=[O:48])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:37])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][O:24][CH:25]3[CH2:30][O:29][C:28]4=[N:31][C:32]([N+:34]([O-:36])=[O:35])=[CH:33][N:27]4[CH2:26]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1.C(OC(=O)COC1C=CC(CO[C@@H]2COC3=NC([N+]([O-])=O)=CN3C2)=CC=1)(C)(C)C.FC1C=C(N2CC(CNC(=O)C)OC2=O)C=CC=1N1CCNCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:38]2[CH2:42][C@H:41]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:40][C:39]2=[O:48])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:37])[CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][O:24][C@@H:25]3[CH2:30][O:29][C:28]4=[N:31][C:32]([N+:34]([O-:36])=[O:35])=[CH:33][N:27]4[CH2:26]3)=[CH:21][CH:22]=2)[CH2:12][CH2:13]1

Participants

9

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18939356N-[[3-(3-Fluoro-4-(piperazin-1-YL)phenyl)-2-oxooxazolidin-5-YL]methyl]acetamideHCID 68545750HCID 68545750, compoundHCID 68549864HCID 68549864, compound

Product 1

HCID 44242067HCID 44242067, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(S)—N-{3-[3-Fluoro-4-(4-{2-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-phenoxy]-acetyl}-piperazin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide. A solution of [4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxylmethyl)-phenoxy]-acetic acid tert-butyl ester (100 mg, 0.25 mmol) in TFA/CH2Cl2 (2 mL) was stirred at room temperature for 2 h. The resultant mixture was concentrated in vacuo, and diluted with DCM, to the solution was added N-[3-(3-fluoro-4-piperazin-1-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide (50 mg, 0.15 mmol) (prepared by following the procedure disclosed by U.S. Pat. No. 5,547,950 or Brickner 1996), HOBt (21.6 mg, 0.16 mmol), EDCI (30.7 mg, 0.16 mmol) and DIPEA (0.20 ml). The mixture was stirred at room temperature for 24 hours diluted with DCM, washed with sat. NaHCO3, 1 N HCl and sat. NaHCO3, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by preparative TLC plates (5% MeOH in dichloromethane) to give the title product as a solid (6.0 mg, 4%). ESI MS m/z 668.4 (M+H+).

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. additiondiluted with DCM, to the solution
  3. customprepared
  4. washwashed with sat. NaHCO3, 1 N HCl and sat. NaHCO3
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative TLC plates (5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-ecea4fecde974d2aa381629b03466048
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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