Ammonium Chloride → HCID 90314080, compound

HRID 1523961Notes

Reaction equation

HRID 1523961 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]4[C:27](=[C:28]([N+:30]([O-])=O)[CH:29]=3)[NH:26][CH:25]=[CH:24]4)=[C:17]([F:33])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>O.CC(C)=O.[Zn]>[NH2:30][C:28]1[CH:29]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:9]([S:6]([NH:5][C:1]([CH3:3])([CH3:2])[CH3:4])(=[O:8])=[O:7])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:16][C:17]=2[F:33])[CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 90314538HCID 90314538, compound

Product 1

HCID 90314080HCID 90314080, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Zn dust (123 mg, 1.88 mmol) was added to a solution of N-(tert-butyl)-3′-fluoro-4′-(7-nitro-1H-indol-5-yl)-[1,1′-biphenyl]-2-sulfonamide (23 mg, 0.19 mmol) and NH4Cl (101 mg, 1.88 mmol) in water (0.75 mL) and acetone (3.76 mL). The mixture was stirred at rt for 1 hour and then filtered through Celite. The resulting filtrate was concentrated to dryness and then taken up in water and extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and concentrated to dryness to give the title compound (23 mg, 28%). MS (ESI): mass calcd. for C24H24FN3O2S, 437.16; m/z found, 438.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.20 (dd, J=8.0, 1.3, 1H), 8.17-8.10 (m, 1H), 7.63-7.56 (m, 2H), 7.54-7.48 (m, 1H), 7.42 (s, 1H), 7.38 (dd, J=7.8, 1.7, 2H), 7.32 (dd, J=11.4, 1.8, 1H), 6.86 (m, 1H), 6.62 (dd, J=3.2, 2.0, 1H), 3.78-3.68 (m, 2H), 1.05 (s, 9H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe resulting filtrate was concentrated to dryness
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c3192f42b4dd49c58c6831f094f5a16b
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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