Ammonium Chloride → HCID 67255163, compound

HRID 511411Notes

Reaction equation

HRID 511411 reaction equation
[NH2:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[CH2:7][C:6]=2[C:5]([C:13]#[N:14])=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[N:15]=[N:16][NH:17][N:14]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67253846HCID 67253846, compound2×

Product 1

HCID 67255163HCID 67255163, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-Amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carbonitrile (Compound 181B, 25.0 mg, 0.134 mmol), sodium azide (104 mg, 1.60 mmol) and ammonium chloride (85.7 mg, 1.60 mmol) in DMF (6 mL) were mixed and heated in microwave at 120° C. for 9 hours. The crude mixture was filtered and directly purified by MDP to obtain the title compound (12.0 mg, 39% yield). MS (ES+): m/z 231.23 (100) [MH+]; HPLC: tR=0.59 min (UPLC, analytical).

Workup

  1. additionwere mixed
  2. filtrationThe crude mixture was filtered
  3. customdirectly purified by MDP

Sources & evidence

ORD record
ord-5b1d04b0279d4a9f9623bdd049c773e7
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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