Morpholine → (S)-7-(2-fluoropyridin-3-yl)-3-morpholino-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

HRID 336017Notes

Reaction equation

HRID 336017 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][S:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12](Cl)[N:11]=[C:10](F)[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[F:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[F:23][C:24]1[C:29]([C:2]2[CH:3]=[C:4]3[C@@:15]4([CH2:19][S:18][C:17]([NH2:20])=[N:16]4)[C:14]4[CH:13]=[C:12]([N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)[N:11]=[CH:10][C:9]=4[O:8][C:5]3=[CH:6][CH:7]=2)=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 27832702-Fluoropyridine-3-boronic acidHCID 86658508(S)-7-bromo-3-chloro-1-fluoro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 53464319(S)-7-(2-fluoropyridin-3-yl)-3-morpholino-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Procedure

The titled compound was synthesized by steps analogous to those described in Method CC10 above, but using (S)-7-bromo-3-chloro-1-fluoro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazol]-2′-amine (prepared as described in Method BB26 but using 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one), 2-fluoropyridin-3-ylboronic acid and morpholine. MS m/z=450.1 [M+H]+. Calculated for C23H20FN5O2S: 449.13.

Sources & evidence

ORD record
ord-c20e827f09fa4005856a26f04188dbb7
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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