Ammonium Chloride → HCID 178446042, compound

HRID 45410Notes

Reaction equation

HRID 45410 reaction equation
[CH2:1]([O:8][C:9](=[O:44])[NH:10][C@H:11]([C:16](=[O:43])[NH:17][C@@:18]1([C:33](=[O:42])[NH:34][C@H:35]([C:40]#[N:41])[CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:30][C:29]2[C:28]3[C:23](=[C:24]([Cl:32])[CH:25]=[C:26]([Cl:31])[CH:27]=3)[NH:22][C:21]=2[CH2:20][CH2:19]1)[CH:12]([CH3:15])[CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:45]=[N+:46]=[N-:47].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:44])[NH:10][C@H:11]([C:16](=[O:43])[NH:17][C@@:18]1([C:33](=[O:42])[NH:34][C@H:35]([C:40]2[NH:47][N:46]=[N:45][N:41]=2)[CH2:36][CH:37]([CH3:38])[CH3:39])[CH2:30][C:29]2[C:28]3[C:23](=[C:24]([Cl:32])[CH:25]=[C:26]([Cl:31])[CH:27]=3)[NH:22][C:21]=2[CH2:20][CH2:19]1)[CH:12]([CH3:15])[CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67291686{(S)-1-[(R)-6,8-Dichloro-3-((S)-1-cyano-3-methyl-butylcarbamoyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylcarbamoyl]-2-methyl-butyl}-carbamic acid benzyl ester

Product 1

HCID 178446042HCID 178446042, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.122 g (0.19 mmol) of {(5)-1-[(R)-6,8-Dichloro-3-((S)-1-cyano-3-methyl-butylcarbamoyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylcarbamoyl]-2-methyl-butyl}-carbamic acid benzyl ester synthesized according to 84 (see below), 0.028 g (0.44 mmol) of sodium azide and 0.026 (0.48 mmol) of ammonium chloride were heated in 2 mL of DMF in a microwave at 110° C. and 100 watt for 6 h. The reaction solution was separated on a preparative HPLC column.

Workup

  1. customThe reaction solution was separated on a preparative HPLC column

Sources & evidence

ORD record
ord-dd7d7b6d9e3043f59fb9ab8dad77dbe8
Source dataset
uspto-grants-2013_09
Patent number
US08541462B2

Reaction notes

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