Hydrochloric Acid → HCID 90293527、化合物

HRID 1631040ノート

反応式

HRID 1631040 の反応式
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([OH:9])=[O:8].[CH3:10]OC(OC)(C)C.Cl.[Cl:18][C:19]1[C:20](Cl)=[N:21][CH:22]=[C:23]([CH:26]=1)[C:24]#[N:25].CCN(C(C)C)C(C)C>CO.CC#N.C(Cl)Cl>[Cl:18][C:19]1[C:20]([NH:1][C@H:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[C:7]([O:9][CH3:10])=[O:8])=[N:21][CH:22]=[C:23]([C:24]#[N:25])[CH:26]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 73305CispentacinHCID 81531DiisopropylethylamineHCID 128784645,6-Dichloropyridine-3-carbonitrile

生成物 1

HCID 90293527HCID 90293527、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of cis-2-amino-1-cyclopentanecarboxylic acid (0.403 g; 3.12 mmol) and 2,2-dimethoxypropane (3 mL) in MeOH (5 mL) was treated with concentrated hydrochloric acid (2 mL). The reaction mixture was heated under reflux for 8 hours. The solvent was evaporated in vacuo. The residue was combined with 5,6-dichloronicotinonitrile (Bionet, 0.346 g; 2.00 mmol), DIEA (0.348 mL; 2.00 mmol) in MeCN (10 mL). The reaction mixture was heated under reflux for 24 hours. The reaction mixture was diluted with DCM and washed with water. The organic phase was passed through a hydrophobic frit and the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (60 iso-hexane to 10 EtOAc) to afford the title product. 1H NMR (CDCl3, 400 MHz) δ 8.29 (1H, d, J=2 Hz), 7.61 (1H, d, J=2 Hz), 6.29 (1H, br d, J=7.6 Hz), 4.76-4.68 (1H, m), 3.63 (3H, s), 3.16-3.10 (1H, m), 2.16-1.78 (6H, m).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customThe solvent was evaporated in vacuo
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 24 hours
  6. washwashed with water
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica
  9. washeluting with iso-hexane/EtOAc (60 iso-hexane to 10 EtOAc)

出典と根拠

ORDレコード
ord-da6dac7911634a7fbb6210bcc33a66b0
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

反応ノート

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