Diisopropylethylamine → HCID 178458670, 화합물

HRID 450373노트

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HRID 450373 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.[NH2:22][C@H:23]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=1)[CH2:24][OH:25].C(N(C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C@@H:23]([NH:22][C:2]2[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[N:7]=2)[CH2:24][OH:25])=[N:27][CH:28]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 68482269(R)-2-Amino-2-(5-fluoropyridin-2-yl)ethanol hydrochloride2회HCID 178458609HCID 178458609, 화합물2회

생성물 1

HCID 178458670HCID 178458670, 화합물수율 64.2%

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, 0.5 g) and (2R)-2-amino-2-(5-fluoropyridin-2-yl)ethanol hydrochloride (Intermediate 23, 0.45 g) in n-BuOH (10 mL) with diisopropylethylamine (3 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 0.45 g of desired product. MS (electrospray): 418 (M+1) for C18H20FN7O4. 1H NMR (300 MHz, CD3OD) δ ppm 8.50 (s, 1H) 8.20 (d, 1H) 7.60 (s, 1H) 7.45 (s, 1H) 6.30 (s, 1H) 5.70 (s, 1H) 5.45 (m, 1H), 4.60 (m, 1H) 3.90 (m, 2H) 1.30 (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-e9e18ac10239412992d01c4a7dd7a4d4
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486966B2

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