1-Methylpiperazine → HCID 71062179, compound

HRID 529025Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9](=[O:19])[N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])[N:6]=[C:5]1[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].C(N(C(C)C)CC)(C)C.[CH3:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C=O)C.O>[CH2:15]([N:10]([CH2:11][CH2:12][CH2:13][CH3:14])[C:9]([C:7]1[N:6]=[C:5]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=2[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[N:4]([CH2:3][CH2:2][N:53]2[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]2)[CH:8]=1)=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-benzyl 1-methyl 4-(1-(2-chloroethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (120 mg, 0.21 mmol) in dry DMF (2 mL) was added diisopropylethyl amine (26.5 mg, 0.21 mmol) and 1-methylpiperazine (21 mg, 0.21 mmol at room temperature. The reaction mixture was heated at 90° C. for 16 h, diluted with water and extracted with MTBE (3×). The combined organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude product. The crude material was purified by flash chromatography (gradient from 0 to 5% MeOH/CH2Cl2) to provide the title compound (60 mg, 45%). MS(ESI+) m/z 619.2 (M+H)+

Workup

extractionextracted with MTBE (3×)
dry with materialThe combined organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customto give the crude product
customThe crude material was purified by flash chromatography (gradient from 0 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-0d4d208e6ea7479d81292f12faba2983
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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