HCID 11733829, compound → HCID 67081833, compound

HRID 2273530Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[C:18]([OH:19])[C:13]3=[CH:12][N:11]=2)=[O:9])=[CH:4][C:3]=1[O:20][CH3:21].I[CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39]I>>[CH2:23]([O:19][C:18]1[C:13]2[N:14]([C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:20][CH3:21])[CH:4]=3)=[O:9])=[N:11][CH:12]=2)[CH:15]=[CH:16][CH:17]=1)[CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:19][C:18]1[C:13]2[N:14]([C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:20][CH3:21])[CH:4]=3)=[O:9])=[N:11][CH:12]=2)[CH:15]=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 11733829HCID 11733829, compound

HCID 11851868HCID 11851868, compound

Product 1

HCID 67081833HCID 67081833, compoundYield 27%

Procedure

By following the process described in Stage A of Example 8, Example 10 is prepared from (4-amino-3-methoxyphenyl)(8-hydroxyimidazo[1,5-a]pyridin-3-yl)-methanone (described in Patent Application WO2006097625) with 1,17-diiodo-3,6,9,12,15-pentaoxaheptadecane (Example R2). After purification by flash chromatography on silica gel (dichloromethane/acetone gradient=90/10 to 70/30), 0.93 g (27%) of a yellow powder is obtained.

Workup

customAfter purification by flash chromatography on silica gel (dichloromethane/acetone gradient=90/10 to 70/30)

Sources & evidence

ORD record: ord-52fd9b2e33d24c5bbee1c0258a1fb235
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120819B2

Reaction notes

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