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

HRID 1969645ノート

反応式

HRID 1969645 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-154aea258ea54b8e94532b39acb2bddf
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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