Imidazole → HCID 59218142, compound

HRID 2246948Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12](S(C3C=CC(C)=CC=3)(=O)=O)[C@@H:11]([CH2:42][C@H:43](OS(C)(=O)=O)[CH3:44])[CH2:10]2)=[CH:5][CH:4]=1.[NH:50]1[CH:54]=[CH:53][N:52]=[CH:51]1>>[N:50]1([C@@H:43]([CH3:44])[CH2:42][C@@H:11]2[NH:12][CH2:13][C@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[C@@H:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH:54]=[CH:53][N:52]=[CH:51]1

Participants

Reactant 2

HCID 795Imidazole

HCID 86621620HCID 86621620, compound

Product 1

HCID 59218142HCID 59218142, compound

Procedure

Similar to example 42a, methanesulfonic acid (R)-2-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-1-methyl-ethyl ester (from example 38b) are reacted with imidazol to afford the title compound as a colourless oil. Rf=0.22 (dichlormethane-methanol 10:1); Rt=4.60.

Sources & evidence

ORD record: ord-519d836e063745bb8a58847cc7f7ca62
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687495B2

Reaction notes

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