6-Chloro-3-pyridinecarbonitrile → 6-((1-((R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-methylpyrrolidin-3-yl)methylamino)nicotinonitrile

HRID 515128Notes

Reaction equation

HRID 515128 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([C:23]2C=CC=CC=2)[CH2:8][CH2:7][N:6]([CH2:9][C@@H:10]([C:12]2[CH:21]=[CH:20][C:15]3[C:16](=[O:19])[O:17][CH2:18][C:14]=3[C:13]=2[CH3:22])[OH:11])[CH2:5]1.Cl[C:30]1[N:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1>>[OH:11][C@H:10]([C:12]1[C:13]([CH3:22])=[C:14]2[C:15](=[CH:20][CH:21]=1)[C:16](=[O:19])[O:17][CH2:18]2)[CH2:9][N:6]1[CH2:7][CH2:8][C:4]([CH2:3][NH:2][C:30]2[CH:31]=[CH:32][C:33]([C:36]#[N:37])=[CH:34][N:35]=2)([CH3:23])[CH2:5]1

Participants

3

Reactant 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 901905175-((1R)-2-(3-(aminomethyl)-3-phenylpyrrolidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715659446-((1-((R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-methylpyrrolidin-3-yl)methylamino)nicotinonitrile

Procedure

6-((1-((R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-methylpyrrolidin-3-yl)methylamino)nicotinonitrile was prepared in a similar fashion to that described for the synthesis of EXAMPLE 18 starting from 5-[(R)-2-[3-(Aminomethyl)-3-phenylpyrrolidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride [INTERMEDIATE 15] and 6-chloropyridine-3-carbonitrile.

Sources & evidence

ORD record
ord-a3a360ad05a0405e9ecc6be03b1827d7
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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