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

HRID 1527585Notes

Reaction equation

HRID 1527585 reaction equation
[Cl:1][C:2]1[C:3]([F:35])=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][NH:6][C:7]([C@@H:9]1[CH2:14][C@:13]2(CO)[C@@H:11]([CH2:12]2)[N:10]1[C:17](=[O:31])[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:8].[C:36]([O:40]C(N1[C@H](C(=O)N[C@@H](C2C=CC=C(Cl)C=2F)CO)C[C@@H]2[C@H]1C2)=O)(C)(C)C.ClCl.CCOC(C)=O>>[Cl:1][C:2]1[C:3]([F:35])=[C:4]([C@H:5]([NH:6][C:7]([C@@H:9]2[CH2:14][C@@H:13]3[C@@H:11]([CH2:12]3)[N:10]2[C:17](=[O:31])[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:8])[CH2:36][OH:40])[CH:32]=[CH:33][CH:34]=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 68283751(1R,3S,5R)-3-[(S)-1-(3-Chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl esterHCID 86673875Cl2 EtOAc

Product 1

HCID 86673874(1R,3S,5R)-2-[2-(3-Acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-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 (1R,3S,5R)-3-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (prepared as described in Scheme B9). White powder. TLC, Rf (CH2/Cl2/EtOAc 9:1)=0.70; MS (UPLC/MS): 499.3/501.3 [M+H]+, 543.2/545.3 [M+HCOO]−; tR (HPLC conditions a): 3.02 min.

Workup

  1. custom3.02 min.

Sources & evidence

ORD record
ord-f591a7b044144ec192603eb633abff20
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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