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

HRID 541809노트

반응식

HRID 541809 반응식
[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

참가 물질

6

반응물 1

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

생성물 1

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

시약·촉매·용매 4

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-389b1d6cd7e44fc6bb1b1d363cacf357
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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