Triethylamine → HCID 68653423, compound

HRID 2243848Notes

Reaction equation

HRID 2243848 reaction equation
[CH3:1][C:2]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([CH2:40][C:41](O)=[O:42])[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[C:27]([O:31][C:32]([N:34]1[CH2:35][CH2:36][N:37]([CH2:40][C:41]([N:24]2[CH2:25][CH2:26][N:21]([C:18]3[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:2]4([CH3:1])[O:6][C:5]5=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]5[CH2:3]4)=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)=[O:42])[CH2:38][CH2:39]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27356422-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acidHCID 23081132HCID 23081132, compound

Product 1

HCID 68653423HCID 68653423, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-methyl-6-nitro-2-(4-piperazin-1-yl-phenoxymethyl)-2,3-dihydro-imidazo[2,1-b]oxazole (200 mg, 0.34 mmol) and 4-carboxymethyl-piperazine-1-carboxylic acid tert-butyl ester (136 mg, 0.55 mmol) in DMF is treated with TBTU (179.8 mg, 0.55 mmol), triethyl amine (0.23 ml, 1.65 mmol) and stirred for 2 h. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated. The residue is purified by preparative TLC (10% methanol in dichloromethane to give 4-(2-{4-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-phenyl]-piperazin-1-yl}-2-oxo-ethyl)-piperazine-1-carboxylic acid tert-butyl ester as yellow oil (152 mg, 78%). ESI MS m/z 585 (M+H); 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 6.83 (d, J=8.4 Hz, 2H), 6.78 (d, J=8.4 Hz, 2H), 4.48 (d, J=Hz), 4.18 (d, J=Hz, 1H), 4.14-4.02 (m, 2H), 3.82-3.71 (m, 4H), 3.56-3.38 (m, 4H), 2.91 (s, 2H), 2.52-2.42 (m, 4H), 1.75-1.62 (m, 4H), 1.42 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by preparative TLC (10% methanol in dichloromethane

Sources & evidence

ORD record
ord-195ae1c312c84c53958462a57bc34c79
Source dataset
uspto-grants-2010_03
Patent number
US07678791B2

Reaction notes

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