2-Fluoropyridine-3-boronic acid → (S)-2'-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-5H-spiro[thiazole-4,9'-xanthen]-2-amine

HRID 336024Notes

Reaction equation

HRID 336024 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16](O)[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8](Br)=[CH:9][CH:10]=1.[F:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1.Cl.[CH:34]12[CH2:40][CH:37]([NH:38][CH2:39]1)[CH2:36][O:35]2>>[C@H:34]12[CH2:40][C@H:37]([N:38]([C:16]3[CH:15]=[C:14]([F:20])[C:13]4[O:12][C:11]5[C:6](=[CH:7][C:8]([C:29]6[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=6)=[CH:9][CH:10]=5)[C@@:5]5([CH2:4][S:3][C:2]([NH2:1])=[N:22]5)[C:18]=4[CH:17]=3)[CH2:39]1)[CH2:36][O:35]2

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 219143642-Oxa-5-azabicyclo[2.2.1]heptane hydrochlorideHCID 67383112(S)-2-amino-7'-bromo-4'-fluoro-5H-spiro[thiazole-4,9'-xanthen]-2'-ol

Product 1

HCID 67437478(S)-2'-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-5H-spiro[thiazole-4,9'-xanthen]-2-amine

Procedure

The titled compound was synthesized by stpes analogous to those described in method AA20 above, but using (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[thiazole-4,9′-xanthen]-2′-ol (prepared as described in Method BB26 and Example 2 but using 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one), 2-fluoropyridin-3-ylboronic acid and 2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride. MS m/z=479.0 [M+H]+.

Sources & evidence

ORD record
ord-603c0ef5da4f4943a716f67c81acb524
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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