(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate → 5-[(S)-1-(Tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxylic acid ((S)-6-azepan-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-yl)amide

HRID 1913825Notes

Reaction equation

HRID 1913825 reaction equation
[N:1]1([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][C@@H:14]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][N:23]=2)=[O:21])[CH2:13][CH2:12]3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34]OS(C)(=O)=O>>[N:1]1([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][C@@H:14]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:34][C@@H:30]4[CH2:31][CH2:32][CH2:33][O:29]4)=[CH:24][N:23]=2)=[O:21])[CH2:13][CH2:12]3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 18649743(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonateHCID 866458295-hydroxypyridine-2-carboxylic acid ((S)-6-azepan-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-yl)amide

Product 1

HCID 595057685-[(S)-1-(Tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxylic acid ((S)-6-azepan-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-yl)amide

Procedure

According to method F, 5-hydroxypyridine-2-carboxylic acid ((S)-6-azepan-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-yl)amide was alkylated with methanesulfonic acid (S)-1-(tetrahydrofuran-2-yl)methyl ester (DMF, 12 h, 80° C.). The product was thus obtained with the molecular weight of 463.63 (C28H37N3O3); MS (ESI): 464 (M+H+).

Workup

  1. customThe product was thus obtained with the molecular weight of 463.63 (C28H37N3O3)

Sources & evidence

ORD record
ord-246dee9ac1f848ddb9fe53207d7abec0
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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