Triethylamine → 1'-(3-bromo-1H-pyrrolo[3,2-b]pyridine-6-carbonyl)-2-tert-butyl-4,6-dihydrospiro[indazole-5,4'-piperidin]-7(2H)-one

HRID 2403703노트

반응식

HRID 2403703 반응식
Cl.[Br:2][C:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:12]([OH:14])=O)[CH:11]=[C:6]2[NH:5][CH:4]=1.Cl.[C:16]([N:20]1[CH:33]=[C:32]2[C:22]([C:23](=[O:34])[CH2:24][C:25]3([CH2:31]2)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[N:21]1)([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.C(OCC)(=O)C.CN(C)C=O>[Br:2][C:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:12]([N:28]3[CH2:27][CH2:26][C:25]4([CH2:24][C:23](=[O:34])[C:22]5[C:32](=[CH:33][N:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:21]=5)[CH2:31]4)[CH2:30][CH2:29]3)=[O:14])[CH:11]=[C:6]2[NH:5][CH:4]=1

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573370712-tert-butyl-4,6-dihydrospiro[indazole-5,4'-piperidin]-7(2H)-one hydrochloride saltHCID 708961403-bromo-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid hydrochloride

생성물 1

HCID 708961201'-(3-bromo-1H-pyrrolo[3,2-b]pyridine-6-carbonyl)-2-tert-butyl-4,6-dihydrospiro[indazole-5,4'-piperidin]-7(2H)-one수율 71%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 3-bromo-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid hydrochloride (2.75 g, 9.91 mmol) and 2-tert-butyl-4,6-dihydrospiro[indazole-5,4′-piperidin]-7(2H)-one hydrochloride salt (2.95 g, 9.91 mmol) in dichloromethane (30 mL) was added triethylamine (5.52 mL, 39.6 mmol). N,N-dimethylformamide (5 mL) was then added, followed by 1-hydroxybenzotriazole (1.61 g, 11.9 mmol) and 1, (3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (2.28 g, 11.9 mmol). The reaction was allowed to stir at room temperature for 60 hours. The reaction was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-10% methanol/ethyl acetate) gave the title compound (3.39 g, 71%) as a pale brown solid. +ESI (M+1+H) 486.2; 1H NMR (400 MHz, CDCl3, δ): 10.05 (br. s., 1 H), 8.57 (d, J=1.8 Hz, 1 H), 7.87 (d, J=1.8 Hz, 1 H), 7.61 (d, J=2.7 Hz, 1 H), 7.44 (s, 1 H), 3.78 (br. s., 2 H), 3.51 (br. s., 2 H), 2.81 (s, 2 H), 2.65 (s, 2 H), 1.63 (s, 13 H).

후처리

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0-10% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-4dde3c4bb6c84ede8409b522d1d911d4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802688B2

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