Diisopropylethylamine → HCID 11997367, compound

HRID 2245838Notes

Reaction equation

HRID 2245838 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH2:14]Cl)[CH2:7][C:6]1=[O:16].[NH:17]1[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:38])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:19][CH2:18]1.CCN(C(C)C)C(C)C.[OH:48][C:49]1[CH:56]=[CH:55][C:52]([CH2:53][NH2:54])=[CH:51][CH:50]=1>CN(C=O)C>[OH:48][C:49]1[CH:56]=[CH:55][C:52]([CH2:53][NH:54][CH2:2][CH2:3][CH2:4][N:5]2[C:6](=[O:16])[CH2:7][N:8]([CH2:12][CH2:13][CH2:14][N:17]3[CH2:18][CH2:19][CH:20]([O:23][C:24](=[O:38])[NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:21][CH2:22]3)[C:9](=[O:11])[CH2:10]2)=[CH:51][CH:50]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 974724-HydroxybenzylamineHCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterHCID 68681660HCID 68681660, compound

Product 1

HCID 11997367HCID 11997367, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1,4-bis(3-chloropropyl)piperazine-2,5-dione (40 mg, 0.15 mmol; prepared as described in Preparation 7) in DMF (1.5 mL) was added biphenyl-2-ylcarbamic acid piperidin-4-yl ester (44 mg, 0.15 mmol; prepared as described in Preparation 3) and DIPEA (0.078 mL, 0.45 mmol) and the reaction was allowed to stir overnight at room temperature. After overnight, 4-hydroxybenzyl amine (18.5 mg, 0.15 mmol) was added and the reaction heated to 50° C. for 16 hours. Next the reaction mixture was concentrated in vacuo and then dissolved in 1:1 mixture HOAc:H2O (1.5 mL) and purified on reverse-phase silica gel (gradient elution, 10-50% ACN/H2O) to afford the title compound in 10% yield (over 2 step) (13 mg, 0.015 mmol). MS m/z: [M+H+] calcd for C35H43N5O5, 614.4; found, 614.2).

Workup

  1. waitAfter overnight
  2. temperaturethe reaction heated to 50° C. for 16 hours
  3. concentrationNext the reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in 1:1 mixture HOAc
  5. customH2O (1.5 mL) and purified on reverse-phase silica gel (gradient elution, 10-50% ACN/H2O)

Sources & evidence

ORD record
ord-a150732c188d478a942e62ea01a9017b
Source dataset
uspto-grants-2010_03
Patent number
US07683173B2

Reaction notes

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