Diisopropylethylamine → HCID 178458661, 화합물

HRID 450369노트

반응식

HRID 450369 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=2)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1.Cl.[F:22][C:23]1[CH:24]=[N:25][C:26]([C@@H:29]([NH2:31])[CH3:30])=[N:27][CH:28]=1.C(N(C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[N:25][C:26]([C@@H:29]([NH:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=2)[CH3:30])=[N:27][CH:28]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochloride2회HCID 178458609HCID 178458609, 화합물2회

생성물 1

HCID 178458661HCID 178458661, 화합물수율 101.7%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A mixture of 6-chloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridin-2-amine (Intermediate 7, 0.4 g) and [(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amine hydrochloride (Intermediate 15, 0.25 g) in n-BuOH (5 mL) with diisopropylethylamine (1.5 mL) was stirred at 70° C. for 4 hours. The resulting mixture was diluted with ethyl acetate (20 mL), and washed with brine (10 mL×3). The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Hexane/Ethyl acetate) to yield 0.55 g of desired product. MS (electrospray): 403 (M+1) for C17H19FN8O3. 1H NMR (300 MHz, CD3OD) δ ppm 8.40 (s, 2H) 8.10 (d, 1H) 6.15 (d, 1H) 5.60 (s, 1H) 5.35 (m, 1H), 4.60 (m, 1H) 1.50 (d, 3H) 1.20 (d, 6H).

후처리

  1. washwashed with brine (10 mL×3)
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe resulting residue was separated by silica gel column (Hexane/Ethyl acetate)

출처 및 근거

ORD 기록
ord-6ca064f8638d4daab161cf45619c09ac
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486966B2

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