Hydrochloric Acid → HCID 90293527, 화합물

HRID 1631040노트

반응식

HRID 1631040 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

HCID 90293527HCID 90293527, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-da6dac7911634a7fbb6210bcc33a66b0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791142B2

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