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Acetylglycine → 4-[5-(2-Acetylamino-acetylamino)-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1257663
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HRID 1257663 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][N:18]=[C:17]3[N:22]([S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])=[O:26])[CH:23]=[CH:24][C:16]=23)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:34]([NH:37][CH2:38][C:39](O)=[O:40])(=[O:36])[CH3:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[C:20]([NH:21][C:39](=[O:40])[CH2:38][NH:37][C:34](=[O:36])[CH3:35])=[CH:19][N:18]=[C:17]3[N:22]([S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:26])=[O:27])[CH:23]=[CH:24][C:16]=23)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

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반응물 4

HCID 10972AcetylglycineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673232814-(5-Amino-1-benzenesulfonyl 1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 67344922
4-[5-(2-Acetylamino-acetylamino)-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester
수율 99.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(5-amino-1-benzene sulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 2.12 mmol), N-acetylglycine (0.30 g, 2.5 mmol), HBTU (1.0 g, 2.8 mmol) and DIEA (1.1 mL, 6.4 mmol) in DMF (5 mL) was stirred at ambient temperature for 20 h. Diluted with water and the solid was collected by filtration, washed with water and dried in vacuum oven at 50° C. for 20 h to afford 4-[5-(2-Acetylamino-acetylamino)-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (1.20 g, 99%). This intermediate was suspended in acetic acid (6 mL) and heated at 100° C. for 7 h. Cooled, diluted with DCM and stirred over aqueous sodium bicarbonate solution. Organic layer separated, washed with water, brine dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 0-10% MeOH/DCM) to afford 4-[2-(acetylamino-methyl)-6-benzenesulfonyl-6H-1,2,3,5,6-tetraaza-as-indacen-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.26 g, 24%): LCMS (Method E, ESI): RT=1.53 min, m+1=553.2.

후처리

  1. filtrationthe solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuum oven at 50° C. for 20 h

출처 및 근거

ORD 기록
ord-7b5a250b8925495c9b5f6ca8175e1b2f
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461328B2

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