2-Methyl-6-(oxiran-2-yl)nicotinonitrile → 6-(1-Hydroxy-2-{10-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9,10-diazatricyclo[4.2.1.12,5]dec-9-yl}ethyl)-2-methylpyridine-3-carbonitrile

HRID 2281340Notes

Reaction equation

HRID 2281340 reaction equation
Cl.[CH:2]12[N:10]([CH2:11][C@@H:12]([C:14]3[CH:23]=[CH:22][C:17]4[C:18](=[O:21])[O:19][CH2:20][C:16]=4[C:15]=3[CH3:24])[OH:13])[CH:7]([CH2:8][CH2:9]1)[CH:6]1[NH:25][CH:3]2[CH2:4][CH2:5]1.[CH3:26][C:27]1[N:34]=[C:33]([CH:35]2[CH2:37][O:36]2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]>>[OH:36][CH:35]([C:33]1[N:34]=[C:27]([CH3:26])[C:28]([C:29]#[N:30])=[CH:31][CH:32]=1)[CH2:37][N:25]1[CH:6]2[CH2:5][CH2:4][CH:3]1[CH:2]1[N:10]([CH2:11][C@H:12]([OH:13])[C:14]3[CH:23]=[CH:22][C:17]4[C:18](=[O:21])[O:19][CH2:20][C:16]=4[C:15]=3[CH3:24])[CH:7]2[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 595687072-Methyl-6-(oxiran-2-yl)nicotinonitrileHCID 895456335-[(1R)-2-(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-1 hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715593716-(1-Hydroxy-2-{10-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9,10-diazatricyclo[4.2.1.12,5]dec-9-yl}ethyl)-2-methylpyridine-3-carbonitrile

Procedure

6-(1-Hydroxy-2-{10-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9,10-diazatricyclo[4.2.1.12,5]dec-9-yl}ethyl)-2-methylpyridine-3-carbonitrile was prepared in a similar fashion to that described for the synthesis of EXAMPLE 1 starting from 5-[(1R)-2-(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-1 hydroxyethyl]-4-methyl-2-benzofuran-1 (3H)-one hydrochloride (INTERMEDIATE 9) and 2-methyl-6-(oxiran-2-yl)nicotinonitrile (PCT Published Application WO 2010/129379).

Sources & evidence

ORD record
ord-d89d795f313d42eea70c0df665a4dcac
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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