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Acetohydrazide → 4-{6-[6-(N'-Acetyl-hydrazinocarbonyl)-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 2189336
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HRID 2189336 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH3:30])=[C:28]([C:31]([OH:33])=O)[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[N:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.[C:73]([NH:76][NH2:77])(=[O:75])[CH3:74].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH3:30])=[C:28]([C:31]([NH:77][NH:76][C:73](=[O:75])[CH3:74])=[O:33])[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

8

반응물 5

HCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580160322-[5-(4-tert-Butoxycarbonyl-piperazin-1-yl)-pyridin-2-ylamino]-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

생성물 1

HCID 58015972
4-{6-[6-(N'-Acetyl-hydrazinocarbonyl)-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester
수율 90.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 12 2-[5-(4-tert-Butoxycarbonyl-piperazin-1-yl)-pyridin-2-ylamino]-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (120 mg, 0.23 mmol), HBTU (130.9 mg, 0.345 mmol) and HOAt (46.97 mg, 0.345 mmol) in dry DMF (15 mL) is added a solution of acetic hydrazide (34.09 mg, 0.46 mmol) and diisopropylethylamine (121 ul, 0.693 mmol) in dry DMF (5 mL). The reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with water and extracted with ethyl acetate three times. The organic layers are combined, washed with brine and dried over anhydrous sodium sulfate. The solvent is evaporated and the crude product is purified by preparative HPLC to give 4-{6-[6-(N′-Acetyl-hydrazinocarbonyl)-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (120 mg, 75.4%). [M+H]+=578.32.

후처리

  1. extractionextracted with ethyl acetate three times
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent is evaporated
  5. customthe crude product is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-05b86a2c8bdb4eb8950758e2e780f815
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08324225B2

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