1-Methylpiperazine → HCID 67155199, compound

HRID 389680Notes

Reaction equation

HRID 389680 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:29][CH2:28][CH2:27][C:26]3=[O:30])[C:20]=2[CH3:31])(=[O:18])=[O:17])[C:12]([OH:14])=O)=[O:8])=[CH:4][CH:3]=1.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[ClH:1].[CH3:31][C:20]1[C:21]([N:25]2[CH2:29][CH2:28][CH2:27][C:26]2=[O:30])=[CH:22][CH:23]=[CH:24][C:19]=1[S:16]([NH:15][C@H:11]([C:12]([N:36]1[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]1)=[O:14])[CH2:10][NH:9][C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:8])(=[O:17])=[O:18]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67155460HCID 67155460, compound

Product 1

HCID 67155199HCID 67155199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 87 (802 mg, 1.65 mmol) was dissolved in 10 ml DCM and N-methyl piperazine (0.73 ml, 6.60 mmol) was added followed by DIPEA (0.55 ml, 3.3 mmol) and TBTU (636 mg, 1.98 mmol). After 1 h stirring at RT the solution was evaporated to dryness and purified by silica gel chromatography. The compound was dissolved in DCM, HCl (2 M in diethyl ether (5 ml)) was added and the solvents were evaporated yielding a white powder. Yield: 651 mg, 70%. MS (ES+): m/e=568.

Workup

  1. customwas evaporated to dryness
  2. custompurified by silica gel chromatography
  3. dissolutionThe compound was dissolved in DCM
  4. additionHCl (2 M in diethyl ether (5 ml)) was added
  5. customthe solvents were evaporated
  6. customyielding a white powder

Sources & evidence

ORD record
ord-5bdfcdb2247c494c915c45fcf6dae182
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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