2-Methyl-3-(oxiran-2-yl)-6-(1H-tetrazol-1-yl)pyridine → 5-[(1R)-1-Hydroxy-2-(4-{2-hydroxy-2-[2-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]ethyl}piperazin-1-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 2281353Notes

Reaction equation

HRID 2281353 reaction equation
Cl.[C@@H:2]12[N:9]([CH2:10][C@@H:11]([C:13]3[C:14]([CH3:23])=[C:15]4[C:19](=[CH:20][CH:21]=3)[C:18](=[O:22])[O:17][CH2:16]4)[OH:12])[C@@H:6](CC1)[CH2:5][NH:4][CH2:3]2.[CH3:24][C:25]1[N:30]=[C:29]([N:31]2[CH:35]=[N:34][N:33]=[N:32]2)[CH:28]=[CH:27][C:26]=1[CH:36]1[CH2:38][O:37]1>>[OH:12][C@H:11]([C:13]1[CH:21]=[CH:20][C:19]2[C:18](=[O:22])[O:17][CH2:16][C:15]=2[C:14]=1[CH3:23])[CH2:10][N:9]1[CH2:2][CH2:3][N:4]([CH2:38][CH:36]([OH:37])[C:26]2[C:25]([CH3:24])=[N:30][C:29]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:28][CH:27]=2)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 895437012-Methyl-3-(oxiran-2-yl)-6-(1H-tetrazol-1-yl)pyridine2×HCID 1176421655-((R)-2-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-8-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 1176421025-[(1R)-1-Hydroxy-2-(4-{2-hydroxy-2-[2-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]ethyl}piperazin-1-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one

Procedure

5-[(1R)-1-Hydroxy-2-(4-{2-hydroxy-2-[2-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]ethyl}piperazin-1-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 34 starting from (R)-5-(1-hydroxy-2-(piperazin-1-yl)ethyl)-4-methylisobenzofuran-1(3H)-one (INTERMEDIATE 12) and 6-methyl-5-(oxiran-2-yl)-2-(1H-tetrazol-1-yl) pyridine (INTERMEDIATE 34).

Sources & evidence

ORD record
ord-7b0f69dffe864471b8101c701e4ea5ee
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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