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Diethylamine → 5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-prop-1-ynyl)-nicotinamide

HRID 1929892
ノート
印刷プレビュー

反応式

HRID 1929892 の反応式
Cl[C:2]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:16][C:5]([C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[OH:15])=[O:7])=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44]([O:47][CH3:48])[C:45]#[CH:46].C(NCC)C>CN(C=O)C.[Cu](I)I>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[C:2]([C:46]#[C:45][CH2:44][O:47][CH3:48])=[N:3][CH:4]=[C:5]([CH:16]=2)[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[OH:15])=[O:7])=[CH:19][CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 693933-MethoxypropyneHCID 866191846-chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

生成物 1

HCID 674260675-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-prop-1-ynyl)-nicotinamide

試薬・触媒・溶媒 2

HCID 83717
Copper iodide
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a mixture of 6-chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide (450 mg), 52 mg bistriphenylphosphinpalladium dichloride, 14 mg copperiodide, 146 mg triphenylphosphine and methyl propargyl ether (0.12 mL) in 10 mL DMF is added diethylamine (1.9 L). The mixture is heated in the microwave oven for 40 min at 120° C. The reaction mixture was cooled to room temperature and partitioned between 1 N hydrochloric acid and ethyl acetate. The organic phase was purified by gradient chromatography on silica gel with heptane:ethyl acetate to yield 0.13 g of the title compound as a light yellow solid, MS (ISP) 399.1 (M+H)−.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between 1 N hydrochloric acid and ethyl acetate
  3. customThe organic phase was purified by gradient chromatography on silica gel with heptane

出典と根拠

ORDレコード
ord-fd26ea3ad52540c489ab3ea4e0415b09
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188093B2

反応ノート

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