Sodium Acetate → 6-[(Z)-[2-(cyclopropylamino)-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-(oxan-4-yloxy)quinoline-3-carbonitrile

HRID 1297744Notes

Reaction equation

HRID 1297744 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[O:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=O.[CH:22]1([NH:25][C:26]2[S:27][CH2:28][C:29](=[O:31])[N:30]=2)[CH2:24][CH2:23]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH:22]1([NH:25][C:26]2[S:27]/[C:28](=[CH:1]\[C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][CH:12]=3)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]4[O:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)/[C:29](=[O:31])[N:30]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 585857836-Formyl-4-((tetrahydro-2H-pyran-4-yl)oxy)quinoline-3-carbonitrileHCID 178516935HCID 178516935, compound

Product 1

HCID 1785102936-[(Z)-[2-(cyclopropylamino)-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-(oxan-4-yloxy)quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Similar procedure as described in example 28c was used, starting from 6-formyl-4-(tetrahydro-pyran-4-yloxy)-quinoline-3-carbonitrile (example 76b), 2-cyclopropylamino-thiazol-4-one (example 37c), sodium acetate and acetic acid to give 6-[2-cyclopropylamino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-(tetrahydropyran-4-yloxy)quinoline-3-carbonitrile. LC-MS m/e 421 (MH+).

Sources & evidence

ORD record
ord-fca3efb34d5a42cca4c78214d58ac169
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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