Ammonium Chloride → 1-benzenesulfonyl-N*4*-((R)-1-benzyl-piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

HRID 1257575노트

반응식

HRID 1257575 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:33]([O-])=O)[C:18]([NH:19][C@@H:20]4[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:33])[C:18]([NH:19][C@@H:20]4[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 58395364(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-((R)-1-benzyl-piperidin-3-yl)amine

생성물 1

HCID 583947461-benzenesulfonyl-N*4*-((R)-1-benzyl-piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine수율 85.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

실험 절차

A mixture of (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-((R)-1-benzyl-piperidin-3-yl)amine (about 0.77 mmol), iron powder (129 mg, 2.31 mmol) and ammonium chloride (206 mg, 3.85 mmol) in ethanol/water (8 ml, 3:1) was heated to reflux for 4 hours. After cooling the mixture was filtered through CELITE®, thoroughly washing the filter cake with ethanol. The filtrate and washings were combined and concentrated under vacuum. The resulting residue was partitioned between ethyl acetate and water, and the organic layer dried with sodium sulfate and concentrated under vacuum. Purification by column chromatography on silica gel (gradient: 0 to 10% methanol in DCM) gave a residue, which was purified by column chromatography on silica gel (gradient: 0 to 5% methanol in ethyl acetate) affording 303 mg (84%) of 1-benzenesulfonyl-N*4*-((R)-1-benzyl-piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine. LCMS (Method B, ESI): RT=2.48-2.68 min, m+H=462.6; 1H NMR (400 MHz, CDCl3) δ: 8.12-8.08 (m, 2H), 7.79 (s, 1H), 7.55-7.49 (m, 1H), 7.46-7.38 (m, 3H), 7.37-7.22 (m, 5H), 6.47 (s, 1H), 5.32-5.26 (br m, 1H), 4.00-3.87 (br m, 1H), 3.58-3.46 (br m, 2H), 2.94-2.28 (br m, 6H), 1.82-1.67 (br m, 2H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered through CELITE®
  5. washthoroughly washing the filter cake with ethanol
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was partitioned between ethyl acetate and water
  8. dry with materialthe organic layer dried with sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customPurification by column chromatography on silica gel (gradient: 0 to 10% methanol in DCM)
  11. customgave a residue, which
  12. customwas purified by column chromatography on silica gel (gradient: 0 to 5% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-fc01f74ebdd84098a1569f96d8f93c60
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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