(1R,3S,5S)-2-[2-(3-acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide → (2S,4R)-1-[2-(3-Acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-4-fluoro-4-methyl-pyrrolidine-2-carboxylic acid [(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethyl]-amide

HRID 1527586Notes

Reaction equation

HRID 1527586 reaction equation
ClC1C(F)=C(C=CC=1)CNC([C@@H]1C[C@]2(CO)[C@@H](C2)N1C(=O)[CH2:18][N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[C:21]([C:28](=[O:30])[CH3:29])=[CH:20]1)=O.C(O[C:41]([N:43]1[CH2:47][C@@:46]([F:49])([CH3:48])[CH2:45][C@H:44]1[C:50](=[O:63])[NH:51][C@@H:52]([C:55]1[CH:60]=[CH:59][CH:58]=[C:57]([Cl:61])[C:56]=1[F:62])[CH2:53][OH:54])=[O:42])(C)(C)C.ClCl.CCOC(C)=O>>[Cl:61][C:57]1[C:56]([F:62])=[C:55]([C@H:52]([NH:51][C:50]([C@@H:44]2[CH2:45][C@:46]([F:49])([CH3:48])[CH2:47][N:43]2[C:41](=[O:42])[CH2:18][N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[C:21]([C:28](=[O:30])[CH3:29])=[CH:20]2)=[O:63])[CH2:53][OH:54])[CH:60]=[CH:59][CH:58]=1

Participants

4

Reactant 3

HCID 68283700(1R,3S,5S)-2-[2-(3-acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamideHCID 68283867(2S,4R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86673875Cl2 EtOAc

Product 1

HCID 71042601(2S,4R)-1-[2-(3-Acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-4-fluoro-4-methyl-pyrrolidine-2-carboxylic acid [(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethyl]-amide

Procedure

The title compound was prepared in 2 steps according to the procedure described for the preparation of Example 610 (1R,3S,5S)-2-[2-(3-acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide from (2S,4R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared using similar protocols as described in Scheme B9). White powder. TLC, Rf (CH2/Cl2/EtOAc 9:1)=0.60; MS (UPLC/MS): 519.3/521.3 [M+H]+, 563.3/565.3 [M+HCOO]−; tR (HPLC conditions a): 2.96 min.

Workup

  1. custom2.96 min.

Sources & evidence

ORD record
ord-5d69d3314fa748f2843ba047d4b8510d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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