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Diisopropylethylamine → (R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate

HRID 1923891
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HRID 1923891 반응식
[Br:1][C:2]1[C:3](F)=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:13][N:14]([C@@H:22]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]1)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(N(C(C)C)C(C)C)C>CN1C(=O)CCC1>[NH2:11][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[C:3]=2[N:24]2[CH2:25][CH2:26][CH2:27][C@@H:22]([N:14]([CH3:13])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:23]2)[NH:8][CH:9]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 28875356tert-Butyl methyl((3R)-piperidin-3-yl)carbamateHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

생성물 1

HCID 67045616(R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
125 °C

실험 절차

A 250 mL round bottom flask was charged with 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (1.00 g, 4.35 mmol; Example 1, Step H), (R)-tert-butyl methyl(piperidin-3-yl)carbamate (1.86 g, 8.69 mmol), N-ethyl-N-isopropylpropan-2-amine (2.27 mL, 13.0 mmol), and NMP (10.8 mL). Nitrogen was bubbled through the mixture for 5 minutes. The reaction was stirred at 125° C. (oil bath) under positive nitrogen atmosphere for 20 hours to provide the crude (R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate.

후처리

  1. customNitrogen was bubbled through the mixture for 5 minutes

출처 및 근거

ORD 기록
ord-d50052e930b849ed84d8b86b97507edb
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178131B2

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