Sodium Acetate → 6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-(tetrahydro-pyran-4-yloxy)-quinoline-3-carbonitrile

HRID 1297741Notes

Reaction equation

HRID 1297741 reaction equation
C([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.COC1C=CC(/[CH:36]=[C:37]2/[C:38]([NH:40][C:41]([S:43]/2)=[NH:42])=[O:39])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:42][C:41]1[S:43]/[C:37](=[CH:36]\[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]3[O:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)/[C:38](=[O:39])[N:40]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 585857836-Formyl-4-((tetrahydro-2H-pyran-4-yl)oxy)quinoline-3-carbonitrileHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 116609026-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-(tetrahydro-pyran-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), pseudothiohydantoin, sodium acetate and acetic acid to give 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-(tetrahydro-pyran-4-yloxy)-quinoline-3-carbonitrile. LC-MS m/e 381 (MH+).

Sources & evidence

ORD record
ord-0048a668b27f47659bd5219091079d3a
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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