2-(Oxan-2-yloxy)ethan-1-ol → (racemic) 6-amino-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)nicotinonitrile

HRID 1777984Notes

Reaction equation

HRID 1777984 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[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH2:18][CH2:19][OH:20].NC1C=C(O[C@H](C)COC)C(C#N)=CN=1>>[NH2:1][C:2]1[CH:9]=[C:8]([O:20][CH2:19][CH2:18][O:17][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 1180369016-Amino-4-fluoronicotinonitrileHCID 118036909(R)-6-amino-4-((1-methoxypropan-2-yl)oxy)nicotinonitrile

Product 1

HCID 118036947(racemic) 6-amino-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)nicotinonitrile

Procedure

From intermediate 21 and (racemic) 2-((tetrahydro-2H-pyran-2-yl)oxy)ethanol, reacted in an analogous manner to the preparation of intermediate 146. (UPLC-MS 7) tR 0.70; ESI-MS 264.1 [M+H]+.

Sources & evidence

ORD record
ord-8ecd740b81894d20b86536c9cc32b453
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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