4-Methylmorpholine → 6-(2-Fluorophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]nicotinamide

HRID 602099

反応式

HRID 602099 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=1.[F:17][C:18]([F:28])([F:27])[CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CCOC(C)=O.O.CC(N(C)C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH:26][CH:23]2[CH2:24][CH2:25][N:20]([CH2:19][C:18]([F:28])([F:17])[F:27])[CH2:21][CH2:22]2)=[O:14])=[CH:10][N:9]=1

参加物

9

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 162287221-(2,2,2-Trifluoroethyl)piperidin-4-amineHCID 247299716-(2-Fluorophenyl)nicotinic acid

生成物 1

HCID 597436546-(2-Fluorophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]nicotinamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

To a vial was added 6-(2-fluorophenyl)nicotinic acid (100 mg, 0.46 mmol), 1-(2,2,2-trifluoroethyl)piperidin-4-amine (83.8 mg, 0.46 mmol), EDAC (97.1 mg, 0.51 mmol), HOBT (62.2 mg, 0.46 mmol), DMA (2 mL) and NMM (0.127 mL, 1.15 mmol). The reaction was stirred for 1 hour at room temperature and then diluted with EtOAc (0.2 mL) followed by H2O (4 mL). The resulting solids were washed in H2O and collected by filtration. 1H NMR (400 MHz, DMSO-d6) □ ppm 9.11 (1H, d, J=1.9 Hz), 8.52 (1H, d, J=7.5 Hz), 8.28 (1H, dd, J=8.3, 2.3 Hz), 7.94-8.05 (1H, m), 7.90 (1H, dd, J=8.4, 1.5 Hz), 7.50-7.58 (1H, m), 3.72-3.89 (1H, m), 3.19 (2H, q, J=10.3 Hz), 2.95 (2H, d, J=11.9 Hz), 2.40-2.48 (2H, m) 1.82 (2H, d, J=13.1 Hz), 1.52-1.67 (2H, m).

後処理

  1. washThe resulting solids were washed in H2O
  2. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-db925966dc9044da8ec0fab02193d862
出典データセット
uspto-grants-2011_03
特許番号
US07902373B2

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