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Triethylamine → HCID 89813497, 화합물

HRID 2172317
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HRID 2172317 반응식
Cl.[Br:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][NH:17][CH2:18]2.[F:23][C:24]1[S:28][C:27]([NH:29][S:30](N2C=CN=C2)(=[O:32])=[O:31])=[N:26][CH:25]=1.C(N(CC)CC)C>C1COCC1.CCOC(C)=O>[Br:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][N:17]([S:30]([NH:29][C:27]1[S:28][C:24]([F:23])=[CH:25][N:26]=1)(=[O:32])=[O:31])[CH2:18]2
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 89813562HCID 89813562, 화합물2회HCID 89815242HCID 89815242, 화합물2회

생성물 1

HCID 89813497HCID 89813497, 화합물수율 27.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate
용매

실험 절차

A solution of 5-(2-bromo-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (Intermediate D, 0.400 g, 1.019 mmol), N-(5-fluorothiazol-2-yl)-1H-imidazole-1-sulfonamide (Intermediate N, 1.012 g, 4.07 mmol), and triethylamine (2.84 ml, 20.37 mmol) in 3 mL THF was heated to 80° C. for 30 minutes. LC/MS showed product so the reaction mixture was diluted with EtOAc and washed with 1 N citric acid. The organics were dried over MgSO4 and concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(5-fluorothiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (0.150 g, 0.280 mmol). 1H NMR (400 MHz, Acetone-d6) δ ppm: 8.06 (s, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.51-7.57 (m, 1H), 7.24-7.35 (m, 2H), 7.08 (s, 1H), 7.05 (d, J=5.7 Hz, 1H), 4.37 (s, 2H), 3.30-3.39 (m, 2H), 2.47-2.60 (m, 2H)

후처리

  1. washwashed with 1 N citric acid
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-225034cffe60429db41072d809609fdb
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051311B2

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