Veratrylamine → HCID 21884598, compound

HRID 722611Notes

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(Cl)=O)[CH:33]=[CH:32][C:30]=4[N:31]=3)[CH:22]=1)[C:14]2=[O:39])=[O:10])C1C=CC=CC=1.[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[O:50][CH3:51])[CH2:45][NH2:46]>>[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[O:50][CH3:51])[CH2:45][NH:46][C:34]1[CH:33]=[CH:32][C:30]2[N:31]=[C:27]([C:23]3[CH:22]=[C:21]([N:15]4[C:14](=[O:39])[C:13]5[C:17](=[CH:18][CH:19]=[C:11]([C:9]([OH:8])=[O:10])[CH:12]=5)[C:16]4=[O:20])[CH:26]=[CH:25][CH:24]=3)[O:28][C:29]=2[CH:35]=1

Participants

Reactant 2

HCID 79832Veratrylamine

HCID 86600622HCID 86600622, compound

Product 1

HCID 21884598HCID 21884598, 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 3,4-dimethoxybenzylamine (23 mg, 0.14 mmol) the title compound was obtained (17 mg, 33%). 1H NMR (DMSO) δ 9.14(t, 1H), 8.44(dd, 1H), 8.36(m, 2H), 8.29(m, 2H), 8.11(d, 1H), 7.99(dd, 1H), 7.91(d, 1H), 7.85–7.76(m, 2H), 6.97(d, 1H), 6.92–6.85(m, 2H), 4.45(d, 2H), 3.73(s, 3H), 3.71(s, 3H). MS 576.2 m/z (M−H)−.

Sources & evidence

ORD record: ord-e9c60163c41147758df30ad16ad850bf
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

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