Diisopropylethylamine → 4-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid (5-methyl-4-phenyl-thiazol-2-yl)-amide

HRID 2190563

反応式

HRID 2190563 の反応式
Cl[C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C:9]2[S:10][C:11]([CH3:20])=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[O:7])=[CH:4][N:3]=1.Cl.[F:24][C:25]([F:39])([F:38])[C:26]1[CH:27]=[C:28]([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:29]=[CH:30][CH:31]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[CH3:20][C:11]1[S:10][C:9]([NH:8][C:6]([C:5]2[CH:21]=[CH:22][C:2]([N:35]3[CH2:36][CH2:37][CH:32]([C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:38])[F:39])[CH:27]=4)[CH2:33][CH2:34]3)=[N:3][CH:4]=2)=[O:7])=[N:13][C:12]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 33799416-chloro-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)pyridine-3-carboxamideHCID 222528494-(3-Trifluoromethylphenyl)piperidine, HCl

生成物 1

HCID 593179814-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid (5-methyl-4-phenyl-thiazol-2-yl)-amide

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 6-chloro-N-(5-methyl-4-phenyl-thiazol-2-yl)-nicotinamide (50 mg, 0.152 mmol) and anhydrous N-methylpyrrolidinone (10 mL) in a sealed tube was added 4-(3-trifluoromethyl-phenyl)-piperidine hydrochloride (80 mg, 0.30 mmol) followed by diisopropylethylamine (0.11 mL, 0.63 mmol). The mixture was heated in an oil bath at 70° C. overnight. After concentration, the crude was purified by RP-HPLC to give 4-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (5-methyl-4-phenyl-thiazol-2-yl)-amide as an off-white powder. LCMS calcd for C28H25F3N4OS (m/e) 522, obsd 523 (M+H).

後処理

  1. concentrationAfter concentration
  2. customthe crude was purified by RP-HPLC

出典と根拠

ORDレコード
ord-078b12da911f4cd1ac7ec024b44444f8
出典データセット
uspto-grants-2012_12
特許番号
US08324385B2

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