Triethylamine → HCID 178452117, 화합물

HRID 539827노트

반응식

HRID 539827 반응식
Br.[OH:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=[C:5]2[CH:4]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:45][CH:46]1[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH2:47]1>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]([NH:45][CH:46]3[CH2:47][CH2:48][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:50][CH2:51]3)=[O:14])[N:11]=[C:5]2[CH:4]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178419750HCID 178419750, 화합물

생성물 1

HCID 178452117HCID 178452117, 화합물수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of 7-hydroxyimidazo[1,2-a]pyridine-2-carboxylic acid hydrobromide salt (0.24 g, 0.93 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added triethylamine (0.22 g, 2.2 mmol), 1-hydroxybenzotriazole hydrate (0.16 g, 1.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23 g, 1.2 mmol), and tert-butyl 4-aminopiperidine-1-carboxylate (0.24 g, 1.2 mmol). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue obtained was purified by flash chromatography (silica gel, ethyl acetate/hexanes=1/1) to afford tert-butyl 4-(7-hydroxyimidazo[1,2-a]pyridine-2-carboxamido)piperidine-1-carboxylate as an off-white solid (0.27 g, 81%). 1H-NMR (CDCl3, 300 MHz): δ 7.93 (m, 2H), 7.31 (m, 1H), 7.25 (m, 1H), 6.85 (m, 1H), 6.65 (m, 1H), 4.08 (m, 3H), 3.13 (m, 2H), 2.93 (m, 2H), 1.97 (m, 2H), 1.44 (s, 9H) ppm; MS (ESI): 361.1 (M+1).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by flash chromatography (silica gel, ethyl acetate/hexanes=1/1)

출처 및 근거

ORD 기록
ord-2eb523d0c38448008800f72cd90b8663
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871770B2

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