1-Piperonylpiperazine → HCID 21884611, compound

HRID 722608Notes

Reaction equation

C([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[N:15]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[O:28][C:29]4[CH:35]=[C:34]([C:36](Cl)=[O:37])[CH:33]=[CH:32][C:30]=4[N:31]=3)[CH:22]=1)[C:14]2=[O:39])=[O:10])C1C=CC=CC=1.[CH2:40]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)[C:41]1[CH:49]=[CH:48][C:47]2[O:46][CH2:45][O:44][C:43]=2[CH:42]=1>>[CH2:40]([N:50]1[CH2:55][CH2:54][N:53]([C:36]([C:34]2[CH:33]=[CH:32][C:30]3[N:31]=[C:27]([C:23]4[CH:22]=[C:21]([N:15]5[C:14](=[O:39])[C:13]6[C:17](=[CH:18][CH:19]=[C:11]([C:9]([OH:10])=[O:8])[CH:12]=6)[C:16]5=[O:20])[CH:26]=[CH:25][CH:24]=4)[O:28][C:29]=3[CH:35]=2)=[O:37])[CH2:52][CH2:51]1)[C:41]1[CH:49]=[CH:48][C:47]2[O:46][CH2:45][O:44][C:43]=2[CH:42]=1

Participants

Reactant 2

HCID 944261-Piperonylpiperazine

HCID 86600622HCID 86600622, compound

Product 1

HCID 21884611HCID 21884611, compound

Procedure

Prepared by the method of Example 76 g), from 2-[3-(6-chlorocarbonylbenzoxazol-2-yl)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid benzyl ester (50 mg, 0.09 mmol) and 1-piperonylpiperazine (31 mg, 0.14 mmol) the title compound was obtained (32 mg, 54%). 1H NMR (DMSO) δ 8.33(dd, 1H), 8.25(m, 2H), 8.17(dt, 1H), 8.01(d, 1H), 7.79–7.65(m, 4H), 7.37(d, 1H), 6.77–6.72(m, 2H), 6.64(dd, 1H), 5.88(s, 2H) 3.45(s, 2H), 3.40–3.2(bm, 4H) 2.48–2.22(bm, 4H). MS 629.2 m/z (M−H)−.

Sources & evidence

ORD record: ord-3d6bab282d5f45c298f6d71e43ee512f
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

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