Iodoethane → N-((1R*,2R*)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-5-ethyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxamide hydrochloride

HRID 2104442노트

반응식

HRID 2104442 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][NH:27][CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2.[CH2:32](N(CC)CC)[CH3:33].C(I)C>CN(C)C=O.Cl>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][N:27]([CH2:32][CH3:33])[CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 68451909N-((1R*,2R)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride

생성물 1

HCID 68449215N-((1R*,2R*)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-5-ethyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxamide hydrochloride

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매

실험 절차

The compound (500 mg) obtained in Example 23 was dissolved in N,N-dimethylformamide (10 mL), and triethylamine (576 μl) and ethyl iodide (329 μl) were added, followed by stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water was added to the residue to collect insoluble matter by filtration. This product was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a pale brown foamy substance. This substance was suspended in 1N hydrochloric acid (2 mL), and the suspension was concentrated under reduced pressure to give the title compound (180 mg).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. customto collect insoluble matter
  4. filtrationby filtration
  5. customThis product was purified by silica gel column chromatography (methylene chloride:methanol=100:3)
  6. customto give a pale brown foamy substance
  7. concentrationthe suspension was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-458b49749bdd481bb2520077e753eeef
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576135B2

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