Carbamic acid, 4-pyridinyl-, 4-nitrophenyl ester → (R)-N-(Pyridin-4-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445277

反応式

HRID 445277 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[N:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=O)[O:29]C2C=CC([N+]([O-])=O)=CC=2)=[CH:23][CH:22]=1>CC#N>[N:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:29])=[CH:23][CH:22]=1

参加物

4

反応物 2

HCID 10355188Carbamic acid, 4-pyridinyl-, 4-nitrophenyl esterHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 59536398(R)-N-(Pyridin-4-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
55 °C

実験手順

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (200 mg, 0.721 mmol) in MeCN (3 mL) was added 4-nitrophenyl pyridin-4-ylcarbamate (561 mg, 2.164 mmol). The resulting mixture was heated to 55° C. overnight. After cooling down to RT the white precipitated obtained was filtered off and washed with DCM (2×1 mL). The combined filtrates were then concentrated and the residue purified by silica gel flash column chromatography (0%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 398 (M+H).

後処理

  1. temperatureAfter cooling down to RT the
  2. customwhite precipitated
  3. customobtained
  4. filtrationwas filtered off
  5. washwashed with DCM (2×1 mL)
  6. concentrationThe combined filtrates were then concentrated
  7. customthe residue purified by silica gel flash column chromatography (0%-100% EtOAc/hexane)

出典と根拠

ORDレコード
ord-52b057d0de864447b934fff0ed6b9904
出典データセット
uspto-grants-2013_07
特許番号
US08476297B2

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