Ammonium Chloride → HCID 178433661, compound

HRID 2233942Notes

Reaction equation

HRID 2233942 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([O:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[C:20]([Cl:26])[N:19]=2)[CH2:14][CH2:13]1)=[O:10].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([O:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[C:22]([C:24]3[NH:29][N:28]=[N:27][N:25]=3)[CH:21]=[C:20]([Cl:26])[N:19]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 866082941-(6-Chloro-4-cyanopyridin-2-yl)piperidin-4-yl 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 178433661HCID 178433661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1-(6-Chloro-4-cyanopyridin-2-yl)piperidin-4-yl 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylate (Example 308, 64 mg, 0.154 mmol), sodium azide (12 mg, 0.185 mmol) and ammonium chloride (8.3 mg, 0.154 mmol) were dissolved in anhydrous DMF (2 ml) and the mixture was heated at 120° C. for 8 h. The mixture was filtered and purified my semi-preparative reverse phase HPLC eluting with CH3CN/H2O (0.1% TFA) (48 mg).

Workup

  1. filtrationThe mixture was filtered
  2. custompurified my semi-preparative reverse phase HPLC
  3. washeluting with CH3CN/H2O (0.1% TFA) (48 mg)

Sources & evidence

ORD record
ord-08f34756443649acb495a099b66f7f02
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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