Methanol → HCID 10120964, compound

HRID 2307715Notes

Reaction equation

[CH:1]1[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=2[CH:4]=[C:3]2[C:12]([O:14][C:15](=[O:16])[C:2]=12)=[O:13])=[O:8].C(N(C(C)C)CC)(C)C.[O:26]([C:33]1[CH:34]=[C:35]([CH:48]=[CH:49][CH:50]=1)[CH2:36][NH:37][C@@H:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40][CH2:39]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:51][OH:52]>>[CH3:51][O:52][C:7]([C:6]1[CH:1]=[C:2]([C:15]([N:37]([CH2:36][C:35]2[CH:48]=[CH:49][CH:50]=[C:33]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:34]=2)[C@@H:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40][CH2:39]2)=[O:16])[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]=1[C:10]([OH:9])=[O:11])=[O:8]

Participants

Reactant 4

HCID 887Methanol

HCID 6966Pyromellitic dianhydride

HCID 81531Diisopropylethylamine

HCID 69721319HCID 69721319, compound

Product 1

HCID 10120964HCID 10120964, compoundYield 21%

Procedure

1,2,4,5-Benzenetetracarboxylic dianhydride (13.8 mmol), diisopropylethyl amine, N-(3-phenoxybenzyl)-N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amine and methanol were processed as described in Example 100. The residue was purified by flash chromatography (silica gel, 95:5 CH2Cl2:methanol to 8:2 CH2Cl2:methanol) to provide the title compounds as an off-white solid (120 mg, 21% yield).

Workup

customThe residue was purified by flash chromatography (silica gel, 95:5 CH2Cl2:methanol to 8:2 CH2Cl2:methanol)

Sources & evidence

ORD record: ord-ccd1e68320dc4ef2bb96333b40027379
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831193B2

Reaction notes

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