(S)-(+)-3-Hydroxytetrahydrofuran → (S)-6-amino-4-((tetrahydrofuran-3-yl)oxy)nicotinonitrile

Reaction equation

[NH2:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[O:11]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12]1>>[NH2:1][C:2]1[CH:9]=[C:8]([O:16][C@H:13]2[CH2:14][CH2:15][O:11][CH2:12]2)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

HCID 1180369016-Amino-4-fluoronicotinonitrile

Product 1

HCID 118036650(S)-6-amino-4-((tetrahydrofuran-3-yl)oxy)nicotinonitrile

Procedure

From intermediate 21 and (S)-tetrahydrofuran-3-ol, reacted in an analogous manner to the preparation of intermediate 47. (UPLC-MS 3) tR 0.48 min; ESI-MS 206.1 [M+H]+.

Sources & evidence

ORD record: ord-13dfce3f58db4c9bb59329d79f36a568
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266883B2

Reaction notes

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