1-Methylpiperazine → HCID 69202712, compound

HRID 2377299Notes

Reaction equation

HRID 2377299 reaction equation
[O:1]([CH2:8][C:9]#[C:10][C:11]1[S:15][CH:14]=[C:13]([C:16]2[C:20]3[CH2:21][C:22]4[N:23]=[CH:24][C:25]([C:28](O)=[O:29])=[CH:26][C:27]=4[C:19]=3[NH:18][N:17]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>ClCCl.CN(C)C(=O)C>[CH3:42][N:43]1[CH2:48][CH2:47][N:46]([C:28]([C:25]2[CH:24]=[N:23][C:22]3[CH2:21][C:20]4[C:16]([C:13]5[CH:12]=[C:11]([C:10]#[C:9][CH2:8][O:1][C:2]6[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=6)[S:15][CH:14]=5)=[N:17][NH:18][C:19]=4[C:27]=3[CH:26]=2)=[O:29])[CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 27960291-Hydroxybenzotriazole hydrateHCID 69203023HCID 69203023, compound

Product 1

HCID 69202712HCID 69202712, compound

Reagents, catalysts & solvents 1

HCID 85741463dichloromethane N,N-dimethylacetamideSolvent

Procedure

A mixture of Example 1094D (68 mg, 0.16 mmol), N-cyclohexylcarbodiimide-N′-methyl polystyrene (1.0 g, 1.28 mmol) and 1-hydroxybenzotriazole hydrate (44 mg, 0.33 mmol) in (2:1) dichloromethane/N,N-dimethylacetamide (10 mL) was agitated for about 15 min. 1-Methylpiperazine (77 mg, 0.77 mmol) was added, the mixture was agitated at room temperature for about 18 h, filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using dichloromethane/methanol/ammonium hydroxide (100:8:0.1) as the mobile phase to provide the title compound. 1H NMR (500 MHz, DMSO-d6): δ 2.23 (s, 3H), 2.39 (m, 4H), 3.40 (m, 2H), 3.63 (m, 2H), 3.97 (s, 2H), 5.09 (s, 2H), 7.03 (m, 3H), 7.38 (m, 2H), 7.80 (s, 1H), 8.01 (m, 2H), 8.41 (s, 1H), 13.41 (s, 1H).MS (ESI): m/z 496 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-c5a217b6fd0d4bbd843291f3e89cacea
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…