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N-methyl-2-pyrrolidone → 2-Acetyl-N-((R)-1-(2-fluoro-5-methyl-4-(methylsulfonamido)phenyl)ethyl)-5,6,7,8-tetrahydroquinoline-6-carboxamide

HRID 1690801
ノート
印刷プレビュー

反応式

HRID 1690801 の反応式
Cl.[NH2:2][C@@H:3]([C:5]1[C:10]([F:11])=[CH:9][C:8]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:7]([CH3:17])[CH:6]=1)[CH3:4].[C:18]([C:21]1[CH:30]=[CH:29][C:28]2[CH2:27][CH:26]([C:31](O)=[O:32])[CH2:25][CH2:24][C:23]=2[N:22]=1)(=[O:20])[CH3:19].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN1CCCC1=O.C(N(CC)C(C)C)(C)C>CCOC(C)=O>[C:18]([C:21]1[CH:30]=[CH:29][C:28]2[CH2:27][CH:26]([C:31]([NH:2][C@@H:3]([C:5]3[CH:6]=[C:7]([CH3:17])[C:8]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:10]=3[F:11])[CH3:4])=[O:32])[CH2:25][CH2:24][C:23]=2[N:22]=1)(=[O:20])[CH3:19]
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 5

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581186172-Acetyl-5,6,7,8-tetrahydroquinoline-6-carboxylic acidHCID 66718598(R)-N-(4-(1-aminoethyl)-5-fluoro-2-methylphenyl)methanesulfonamide hydrochloride

生成物 1

HCID 58118630
2-Acetyl-N-((R)-1-(2-fluoro-5-methyl-4-(methylsulfonamido)phenyl)ethyl)-5,6,7,8-tetrahydroquinoline-6-carboxamide
収率 91.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a mixture of N-[4-((R)-1-Aminoethyl)-5-fluoro-2-methylphenyl]methanesulfonamide hydrochloride (55.3 mg, 0.195 mmol), 2-acetyl-5,6,7,8-tetrahydroquinoline-6-carboxylic acid (45 mg, 0.20 mmol) and N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (110 mg, 0.29 mmol) in N-Methylpyrrolidinone (192 uL, 1.99 mmol), N,N-Diisopropylethylamine (0.10 mL, 0.59 mmol) was added and the reaction was heated at 60° C. 4 h. The crude was diluted with EtOAc and washed with 1N HCl, 1M NaHCO3 and brine. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to afford the title product (80 mg, 90%) as a brown oil that was used without further purification into the next step. m/z=448.4 (M+H)+.

後処理

  1. additionwas added
  2. custom4 h
  3. washwashed with 1N HCl, 1M NaHCO3 and brine
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-dd5737f927464402bd7fcf0d3c1220f7
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08153651B2

反応ノート

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