N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzenesulfonamide → 3-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide

HRID 541809Notes

Reaction equation

HRID 541809 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)(=[O:16])=[O:15])[C:5]([Cl:29])=[CH:4][N:3]=1>O.CO.C(O)(=O)C.[Fe]>[NH2:23][C:19]1[CH:18]=[C:17]([S:14]([NH:13][CH2:12][C:11]2[CH:26]=[CH:27][CH:28]=[C:9]([NH:8][C:6]3[C:5]([Cl:29])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:10]=2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 1

HCID 57961735N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzenesulfonamide

Product 1

HCID 579626943-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamideYield 90%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzenesulfonamide (50.0 mg, 0.11 mmol) in water (0.08 mL), methanol (0.42 mL) and acetic acid (0.17 mL) was added iron (15 mg, 0.28 mmol) powder in small quantities. When the addition was completed, the mixture was stirred in water bath for 3 h and the reaction was complete. The mixture was filtered and the cake was washed with MeOH/EtOAc. The brown filtrate was concentrated and diluted with H2O, and the aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as a light brown powder (42 mg, 90%). LCMS for C17H15Cl2N5O2S (M+H)+: m/z=424.0, 426.0, 428.0. 1H NMR (400 MHz, CD3OD): δ 8.22 (t, J=2.0 Hz, 1H), 8.52 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 7.48 (m, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.28 (m, 1H), 7.20 (t, J=8.0 Hz, 1H), 7.08 (ddd, J=8.4, 2.0, 1.2, 1H), 6.84 (ddd, J=8.0, 1.6, 1.2, 1H), 4.21 (s, 2H).

Workup

  1. additionWhen the addition
  2. filtrationThe mixture was filtered
  3. washthe cake was washed with MeOH/EtOAc
  4. concentrationThe brown filtrate was concentrated
  5. additiondiluted with H2O
  6. extractionthe aqueous layer was extracted with EtOAc three times
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-389b1d6cd7e44fc6bb1b1d363cacf357
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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