4,4-Difluoropiperidine hydrochloride → (S)-3-(3,3-difluoropyrrolidin-1-yl)-1-fluoro-7-(2-fluoropyridin-3-yl)-5'-H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 336002Notes

Reaction equation

HRID 336002 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12](Cl)[N:11]=[C:10]([F:22])[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.Cl.[F:34][C:35]1([F:41])[CH2:40][CH2:39][NH:38][CH2:37]C1>>[F:41][C:35]1([F:34])[CH2:37][N:38]([C:12]2[N:11]=[C:10]([F:22])[C:9]3[O:8][C:5]4[C:4]([C@@:15]5([CH2:19][O:18][C:17]([NH2:20])=[N:16]5)[C:14]=3[CH:13]=2)=[CH:3][C:2]([C:29]2[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:7][CH:6]=4)[CH2:39][CH2:40]1

Participants

4

Reactant 3

HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 27832702-Fluoropyridine-3-boronic acidHCID 58466258(S)-7-bromo-3-chloro-1-fluoro-5'H-spiro[chromeno[2,3-c]pyridine-5,4' oxazol]-2'-amine

Product 1

HCID 53464257(S)-3-(3,3-difluoropyrrolidin-1-yl)-1-fluoro-7-(2-fluoropyridin-3-yl)-5'-H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Procedure

The title compound was synthesized by steps analogous to those described in method CC4 above, but using (S)-7-bromo-3-chloro-1-fluoro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (prepared by steps analogous to those described in Method BB33), 2-fluoropyridin-3-ylboronic acid and 4,4-difluoropiperidine hydrochloride.

Workup

  1. customprepared by steps analogous to

Sources & evidence

ORD record
ord-2a26bb09207e445caf53603825a365eb
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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