Sodium Azide → HCID 178467195, compound

HRID 1527588Notes

Reaction equation

HRID 1527588 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@@H:13]2[C@@H:11]([CH2:12]2)[N:10]1[C:15](=[O:31])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=2)[C:19]([C:28](=[O:30])[CH3:29])=[CH:18]1)=[O:8].[N-:36]=[N+:37]=[N-:38].[Na+]>O.C(O)(C)C.[Br-].[Zn+2].[Br-]>[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@@H:13]2[C@@H:11]([CH2:12]2)[N:10]1[C:15](=[O:31])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]3[NH:38][N:37]=[N:36][N:27]=3)[CH:24]=2)[C:19]([C:28](=[O:30])[CH3:29])=[CH:18]1)=[O:8]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 68284137HCID 68284137, compound

Product 1

HCID 178467195HCID 178467195, compound

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

The title compound was prepared in a similar manner as described above for Example 617 from (1R,3S,5R)-2-[2-(3-acetyl-6-cyano-indol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide (prepared as described in Example 616 (100.0 mg, 0.203 mmol), sodium azide (66.0 mg, 1.014 mmol) and zinc bromide (228.0 mg, 1.014 mmol) in water (2 mL) and isopropanol (1 mL). White solid. MS (LC/MS): 536.0 [M+H]+; tR (HPLC conditions k): 3.21 min.

Workup

  1. customprepared
  2. custom3.21 min.

Sources & evidence

ORD record
ord-f057bc8e1cf04862996eb0fdc2df455b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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