(3-Acetyl-indol-1-yl)-acetic acid → (1R,3S,5S)-2-[2-(3-Acetyl-indol-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide

HRID 1527583Notes

Reaction equation

HRID 1527583 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([CH2:15][OH:16])[C@@H:11]([CH2:12]2)[N:10]1[C:17](=[O:31])[CH2:18][N:19]1[C:23]2=N[CH:25]=[CH:26][CH:27]=[C:22]2[C:21]([C:28](=[O:30])[CH3:29])=[CH:20]1)=[O:8].[C:36](C1C2C(=CC=CC=2)N(CC(O)=O)C=1)(=O)C>CCOC(C)=O>[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([CH2:15][OH:16])[C@@H:11]([CH2:12]2)[N:10]1[C:17](=[O:31])[CH2:18][N:19]1[C:23]2[C:22](=[CH:27][CH:26]=[CH:25][CH:36]=2)[C:21]([C:28](=[O:30])[CH3:29])=[CH:20]1)=[O:8]

Participants

4

Reactant 2

HCID 1088616(3-Acetyl-indol-1-yl)-acetic acidHCID 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-benzylamide

Product 1

HCID 68284528(1R,3S,5S)-2-[2-(3-Acetyl-indol-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 using (3-acetyl-indol-1-yl)-acetic acid instead of (3-acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetic acid. White powder. TLC, Rf (EtOAc)=0.05; MS (LC/MS): 498/500 [M+H]+, 520/522 [M+Na]+; tR (HPLC conditions f): 1.84 min.

Workup

  1. custom1.84 min.

Sources & evidence

ORD record
ord-5f6886f126af4e1c83f2f4024a33ab2a
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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