Peptide oostatic hormone → N-(3-ethyl-4-(6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide

HRID 1969645노트

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HRID 1969645 반응식
[NH2:1][C:2]1[C:3]([NH:21][CH:22]2[CH:26]([CH2:27][CH3:28])[CH2:25][CH:24]([NH:29][S:30]([CH:33]3[CH2:35][CH2:34]3)(=[O:32])=[O:31])[CH2:23]2)=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH3:36][C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)CC2C=CC(O)=CC=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O>CO.CCOC(C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:27]([CH:26]1[CH:22]([N:21]2[C:3]3=[C:4]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=5)(=[O:12])=[O:13])[C:5]4=[N:6][CH:7]=[C:2]3[N:1]=[CH:36]2)[CH2:23][CH:24]([NH:29][S:30]([CH:33]2[CH2:35][CH2:34]2)(=[O:31])=[O:32])[CH2:25]1)[CH3:28]

참가 물질

6

반응물 2

HCID 5488810Peptide oostatic hormoneHCID 67997957N-(3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide

생성물 1

HCID 67998812N-(3-ethyl-4-(6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide수율 100.1%

시약·촉매·용매 3

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

To a solution of N-(3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.095 g, 75% purity, 0.142 mmol, prepared using L from Preparation #27 and Preparation #000.1 with DIEA, K.1 with TsCl and NaH, and BBB) and TMOF (0.016 mL, 0.147 mmol) in MeOH (3.09 mL) was added toluene-4-sulfonic acid hydrate (0.0003 g, 0.0015 mmol). The reaction was heated at about 65° C. for about 14 h. The reaction was cooled to ambient temperature and concd under reduced pressure to give a crude solid. The solid was dissolved in EtOAc (10 mL) and was washed with saturated aqueous NaHCO3 (5 mL), water (5 mL), and brine (5 mL). The organic portion was separated and dried over anhydrous MgSO4, filtered, and concd under reduced pressure to afford N-(3-ethyl-4-(6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide (0.075 g, 99%) as a yellow solid: LC/MS (Table 1, Method a) Rt=2.15 min; MS m/z: 514 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. customconcd under reduced pressure to give a crude solid
  3. washwas washed with saturated aqueous NaHCO3 (5 mL), water (5 mL), and brine (5 mL)
  4. customThe organic portion was separated
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-154aea258ea54b8e94532b39acb2bddf
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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