6-Aminophthalide → N-(5-(6-(3-Oxo-1,3-dihydroisobenzofuran-5-ylamino)pyrazin-2-yloxy)naphthalen-1-yl)acetamide

HRID 16313Notes

Reaction equation

HRID 16313 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[C:18]3[C:13](=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH2:23][C:24]1[CH:32]=[C:31]2[C:27]([CH2:28][O:29][C:30]2=[O:33])=[CH:26][CH:25]=1>>[O:33]=[C:30]1[C:31]2[C:27](=[CH:26][CH:25]=[C:24]([NH:23][C:2]3[N:3]=[C:4]([O:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[C:18]=4[CH:17]=[CH:16][CH:15]=[C:14]5[NH:19][C:20](=[O:22])[CH3:21])[CH:5]=[N:6][CH:7]=3)[CH:32]=2)[CH2:28][O:29]1

Participants

3

Reactant 2

HCID 936316-AminophthalideHCID 59343448HCID 59343448, compound

Product 1

HCID 24878672N-(5-(6-(3-Oxo-1,3-dihydroisobenzofuran-5-ylamino)pyrazin-2-yloxy)naphthalen-1-yl)acetamideYield 4%

Procedure

Method JJ. This method is identical to Method II, but uses microwave heating. Using Method JJ (heating time: 30 minutes) with 2-chloro-6-(5-acetamidonaphtyl-oxy)-pyrazine (150 mg, 0.48 mmol) and 6-amino-1,3-dihydroisobenzofuran-1-one (89 mg, 0.60 mmol), the title compound was obtained (8 mg). Yield: 4%. 1H NMR (250 MHz, DMSO-d6) δ 2.21 (s, 3H), 5.24 (s, 2H), 7.17 (d, 1H, J=8.5 Hz), 7.45-7.51 (m, 3H), 7.63 (d, 1H, J=8.2 Hz), 7.68-7.75 (m, 3H), 7.92 (s, 1H), 7.98 (s, 1H), 8.05 (d, 1H, J=8.7 Hz), 9.92 (bs, 1H), 10.00 (bs, 1H). m/z 427.1 [(M+H)+ calcd for C24H18N4O4 426.1].

Workup

  1. temperatureheating

Sources & evidence

ORD record
ord-8a80767786964a1f9b322217ba342349
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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