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Hydrazine hydrate (1:1) → (2S,4S)-tert-butyl 4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydrazine carbonyl)pyrrolidine-1-carboxylate

HRID 516179
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HRID 516179 반응식
CCN(C(C)C)C(C)C.O.NN.[NH2:13][C:14]1[C:15]2[C:22]([C:23]#[C:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH3:34])[CH:26]=3)=[CH:21][N:20]([C@@H:35]3[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@H:37]([C:47](O)=[O:48])[CH2:36]3)[C:16]=2[N:17]=[CH:18][N:19]=1.CN(C(O[N:58]1[N:66]=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O.C(OCC)(=O)C>[NH2:13][C:14]1[C:15]2[C:22]([C:23]#[C:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH3:34])[CH:26]=3)=[CH:21][N:20]([C@@H:35]3[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[O:41])[C@H:37]([C:47]([NH:58][NH2:66])=[O:48])[CH2:36]3)[C:16]=2[N:17]=[CH:18][N:19]=1
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참가 물질

8

반응물 4

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 89870887(2S,4S)-4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

생성물 1

HCID 89870936
(2S,4S)-tert-butyl 4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydrazine carbonyl)pyrrolidine-1-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

DIPEA (73 μl) and hydrazine monohydrate (46 μl) were added to a solution of (2S,4S)-4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (106 mg) obtained in Step 1 above and TBTU (100 mg) in DMF (2 ml), and the resulting mixture was stirred at room temperature for 10 minutes. Ethyl acetate and water were added to the reaction mixture to separate the organic layer, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-yellow, amorphous substance (93.6 mg). Physical properties: m/z [M+H]+ 522.4

후처리

  1. customto separate the organic layer
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-7af60dc9cd634cb299ffaaaa04208060
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108973B2

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