1-Methylpiperazine → HCID 86599411, compound

HRID 2182617Notes

Reaction equation

HRID 2182617 reaction equation
[F:1][C:2]([F:38])([F:37])[O:3][C:4]1[CH:36]=[CH:35][C:7]([CH2:8][C@:9]23[CH2:16][C@H:15]([NH:17][C:18](=[O:24])[CH2:19][CH2:20][C:21](O)=[O:22])[CH2:14][N:13]2[C:12](=[O:25])[N:11]([C:26]2[CH:31]=[C:30]([Cl:32])[N:29]=[C:28]([Cl:33])[CH:27]=2)[C:10]3=[O:34])=[CH:6][CH:5]=1.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1.C(Cl)CCl>[F:37][C:2]([F:38])([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C@:9]23[CH2:16][C@H:15]([NH:17][C:18](=[O:24])[CH2:19][CH2:20][C:21]([N:43]4[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]4)=[O:22])[CH2:14][N:13]2[C:12](=[O:25])[N:11]([C:26]2[CH:31]=[C:30]([Cl:32])[N:29]=[C:28]([Cl:33])[CH:27]=2)[C:10]3=[O:34])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86599412HCID 86599412, compound

Product 1

HCID 86599411HCID 86599411, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound from Example 66 (0.12 g) in THF (5 mL) was added N-methyl piperazine (50 μL), EDC (0.90 g), HOBt (0.090 g), and DIEA (0.10 mL). After stirring overnight the reaction mixture was concentrated. The residue was dissolved in EtOAc, washed with water and brine, dried (Na2SO4), filtered, concentrated and purified by chromatography (silica gel: 95:5 CH2Cl2: MeOH, Chromatotron) to afford the titled compound (0.10 g). MS (m/z) 657 [MH+]. mp 70° C.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography (silica gel: 95:5 CH2Cl2: MeOH, Chromatotron)

Sources & evidence

ORD record
ord-0a2502a3cb6a475eb6a8bcf426379366
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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