Hydrochloric Acid → HCID 90293527, compound

HRID 1631040Notes

Reaction equation

HRID 1631040 reaction equation
[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

Participants

9

Reactant 5

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

Product 1

HCID 90293527HCID 90293527, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-da6dac7911634a7fbb6210bcc33a66b0
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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