(3R)-3-fluoropyrrolidine hydrochloride → 6-[6-((s)-3-Fluoro-pyrrolidin-1-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

HRID 69182Notes

Reaction equation

HRID 69182 reaction equation
[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][CH:21]=[CH:20]5)=[CH:14][N:15]=3)[N:12]=2)[CH2:3]1.Cl.F[C@H]1CCNC1.Cl.F[C@@H]1CCNC1>>[F:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][CH:21]=[CH:20]5)=[CH:14][N:15]=3)[N:12]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 2759162(3R)-3-fluoropyrrolidine hydrochlorideHCID 16217739(s)-3-Fluoropyrrolidine hydrochlorideHCID 579174286-[6-((R)-3-fluoro-pyrrolidin-1-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

Product 1

HCID 579174906-[6-((s)-3-Fluoro-pyrrolidin-1-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

Procedure

The title compound was prepared in analogy to the compound of Example 124 using (S)-(+)-3-fluoropyrrolidine hydrochloride as starting material instead of (R)-(−)-3-fluoropyrrolidine hydrochloride (tR 3.89 min (conditions 4), MH+=348.2, 1H-NMR in DMSO-d6: 8.84 (m, 1H); 8.29 (m, 1H); 7.92 (m, 2H); 7.81 (d, 1H); 7.75 (m, 1H); 7.49 (dd, 1H); 7.43 (s, 1H); 6.81 (d, 1H); 5.46 (m, 1H); 4.38 (s, 2H); 3.62 (m, 4H); 2.21 (m, 2H)).

Sources & evidence

ORD record
ord-2a330022ffe448429d861fe770a21af8
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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