Dichloromethane → [4-(5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

HRID 51639

반응식

HRID 51639 반응식
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[CH:22][C:21]3[C:20](=O)[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH:15]=2)=[CH:8][C:7]=1[F:27])[CH3:2].ClCCl.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.C([BH3-])#N.[Na+]>CCCCCC.C(OCC)(=O)C.C(O)(=O)C.C(#N)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[CH:22][C:21]3[CH:20]([NH:35][CH:32]4[CH2:34][CH2:33]4)[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH:15]=2)=[CH:8][C:7]=1[F:27])[CH3:2]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 69548870[2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester2회

생성물 1

HCID 69548141[4-(5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

Following general procedure G and using [2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl) phenyl]acetic acid ethyl ester (Compound 14, 0.258 g, 0.68 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL) and sodium cyanoborohydride (0.266 g, 4.23 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20-25% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.21 g, 73%).

출처 및 근거

ORD 기록
ord-c05d2c36124b4a678cc5fec5e58352e6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713647B2

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