Lithium cyanide → N-[6-Chloro-2-[(3S)-3-cyano-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217901Notes

Reaction equation

[C-:1]#[N:2].[Li+].[Cl:4][C:5]1[C:6]([NH:21][C:22](=[O:30])[CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([N:15]1[CH2:19][CH2:18][C@@H:17](O)[CH2:16]1)[CH:9]=[CH:8]2.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:4][C:5]1[C:6]([NH:21][C:22](=[O:30])[CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([N:15]1[CH2:19][CH2:18][C@H:17]([C:1]#[N:2])[CH2:16]1)[CH:9]=[CH:8]2

Participants

Conditions

Temperature: 60 °C

Procedure

Lithium cyanide (4 mL, 0.5M in DMF) was added to N-[6-chloro-2-[(3R)-3-hydroxy-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 33(a)) (0.21 g) in N,N′-dimethylformamide. The reaction mixture was heated at 60° C. for 10 hours. A saturated solution of sodium bicarbonate was added and the reaction mixture extracted with ethyl acetate. The combined organics were washed with brine, dried and concentrated. Purification (SiO2, iso-hexane:ethyl acetate 1:1 as eluant) gave the title compound as a solid (0.066 g).

Workup

extractionthe reaction mixture extracted with ethyl acetate
washThe combined organics were washed with brine
customdried
concentrationconcentrated
customPurification (SiO2, iso-hexane:ethyl acetate 1:1 as eluant)

Sources & evidence

ORD record: ord-d68708df5dd04b3591015a0ca0abe0d0
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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