Ammonium Chloride → HCID 178521905, compound

HRID 2235096Notes

Reaction equation

HRID 2235096 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][CH2:17][N:18]3[S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)(=[O:23])=[O:22])=[CH:14][CH:13]=2)=[O:11])=[CH:5][C:4]=1[C:31]([F:34])([F:33])[F:32])#[N:2].[N-:35]=[N+:36]=[N-:37].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:35]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]3[CH:20]=[C:19]4[C:15]([CH2:16][CH2:17][N:18]4[S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=4)(=[O:22])=[O:23])=[CH:14][CH:13]=3)=[O:11])=[CH:5][C:4]=2[C:31]([F:34])([F:32])[F:33])=[N:2][N:37]=[N:36]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86611323HCID 86611323, compound

Product 1

HCID 178521905HCID 178521905, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide (30 mg, 0.06 mmol) in dimethylformamide (0.8 ml) was treated with sodium azide (71 mg, 1.1 mmol, 18 equiv.) and ammonium chloride (58 mg, 1.1 mmol, 18 equiv.). The solution was flushed with argon, then sealed and irradiated in microwave oven at 170° C. for 1 hour. The mixture was diluted with concentrated NaHCO3 and washed with ethyl acetate. The aqueous phase was acidified with HCl 1N to pH 1, then extracted twice with ethyl acetate. The combined organic phases were dried with Na2SO4 and the solvent evaporated to yield 15 mg (46% yield) of 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(1H-tetrazol-5-yl)-3-trifluoromethyl-phenyl]-amide as an orange foam, MS (ISP): m/e=547.2 (M−H), δH (300 MHz; d6-DMSO) 10.75 (1H, s), 8.41 (1H, s), 8.21 (1H, d), 7.97 (1H, s), 7.61-7.84 (5H, m), 7.56 (1H, t), 7.32 (1H, d), 3.98 (2H, t), 2.95 (2H, t).

Workup

  1. customThe solution was flushed with argon
  2. customsealed
  3. customirradiated in microwave oven at 170° C. for 1 hour
  4. additionThe mixture was diluted with concentrated NaHCO3
  5. washwashed with ethyl acetate
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic phases were dried with Na2SO4
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-8c0970abe0964963aa16e6c6a02d91a6
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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