2,6-Dichloropyrazine → Tert-butyl cis-4-[(6-chloropyrazin-2-yl)oxy]-3-fluoropiperidine-1-carboxylate

HRID 1926651Notes

Reaction equation

HRID 1926651 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C@H:10]1[C@@H:15]([OH:16])[CH2:14][CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11]1.ClC1N=C(OC2CCN(C(OC(C)(C)C)=O)CC2)C=NC=1>>[Cl:8][C:4]1[N:3]=[C:2]([O:16][C@H:15]2[CH2:14][CH2:13][N:12]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:11][C@H:10]2[F:9])[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 3

HCID 785042,6-DichloropyrazineHCID 21906088HCID 21906088, compound2×HCID 40152152tert-butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 86644306Tert-butyl cis-4-[(6-chloropyrazin-2-yl)oxy]-3-fluoropiperidine-1-carboxylate

Procedure

tert-butyl cis-4-[(6-chloropyrazin-2-yl)oxy]-3-fluoropiperidine-1-carboxylate was prepared from 2,6-dichloropyrazine and tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate using the conditions described for the preparation of tert-butyl 4-[(6-chloropyrazin-2-yl)oxy]piperidine-1-carboxylate (Compound 1, Step 3). LRMS (ESI) calculated for C14H19ClFN3O3[M+Na]+, 354.1; found 354.1.

Sources & evidence

ORD record
ord-60ef72da12bc4b66975c8c5c94f94d43
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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