4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 6-(1-Hydroxy-2-((R)-3-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethylamino)pyrrolidin-1-yl)ethyl)nicotinonitrile

HRID 515121Notes

Reaction equation

HRID 515121 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([C:11]2[N:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[OH:10])[CH2:4]1.[CH3:19][C:20]1[C:28]2[CH2:27][O:26][C:25](=[O:29])[C:24]=2[CH:23]=[CH:22][C:21]=1[C@@H:30]1[CH2:32][O:31]1>>[OH:10][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=1)[CH2:8][N:5]1[CH2:6][CH2:7][C@@H:3]([NH:2][CH2:32][C@H:30]([OH:31])[C:21]2[C:20]([CH3:19])=[C:28]3[C:24](=[CH:23][CH:22]=2)[C:25](=[O:29])[O:26][CH2:27]3)[CH2:4]1

Participants

3

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×HCID 904106326-{2-[(3R)-3-aminopyrrolidin-1-yl]-1-hydroxyethyl}pyridine-3-carbonitrile hydrochloride2×

Product 1

HCID 715657916-(1-Hydroxy-2-((R)-3-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethylamino)pyrrolidin-1-yl)ethyl)nicotinonitrile

Procedure

6-(1-Hydroxy-2-((R)-3-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethylamino)pyrrolidin-1-yl)ethyl)nicotinonitrile was prepared in a similar fashion to that described for the synthesis of EXAMPLE 1 starting from 6-{2-[(3R)-3-aminopyrrolidin-1-yl]-1-hydroxyethyl}pyridine-3-carbonitrile hydrochloride [INTERMEDIATE 11] and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one [INTERMEDIATE 2B].

Sources & evidence

ORD record
ord-c98eaa3b73b34a0f962e04403fca1ddb
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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