Chloride → HCID 178473719, compound

HRID 2398436Notes

Reaction equation

HRID 2398436 reaction equation
Br.C(O)(=[O:4])C.[Cl-].C([N:10]1C2[C:14](=[C:15]([OH:20])C=CC=2)[C:13](=[O:21])[CH2:12][CH:11]1CC=O)(=O)C.C1(C2SC(=O)CN=2)C=CC=CC=1.[C:37]1([C:43]2[S:44][C:45](=[O:65])[C:46](=[CH:48][CH2:49][CH:50]3[CH2:59][C:58](=[O:60])[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][C:56]=4[OH:61])[N:51]3[C:62](=[O:64])[CH3:63])[N:47]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>N1C=CC=CC=1>[C:43]([NH:47][CH:46]1[CH:48]2[CH:14]([CH:15]([OH:20])[CH:59]3[CH:50]([CH2:49]2)[N:51]([C:62](=[O:64])[CH3:63])[C:52]2[C:57](=[C:56]([OH:61])[CH:55]=[CH:54][CH:53]=2)[C:58]3=[O:60])[C:13](=[O:21])[C:12]([C:11]([NH2:10])=[O:4])=[C:45]1[OH:65])(=[S:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 312ChlorideHCID 125499042-Phenyl-1,3-thiazol-5(4H)-oneHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 53908642HCID 53908642, compoundHCID 54141981HCID 54141981, compound

Product 1

HCID 178473719HCID 178473719, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting material can be obtained by hydrogenation of 4-oxo-5-methoxy-1,4-dihydro-quinoline-2-acetic acid methyl ester to give 4-oxo-5-methoxy-1,2,3,4-tetrahydroquinoline-2-acetic acid methyl ester, saponification to give the free acid, acetylation to give 1-acetyl-4-oxo-5-methoxy-1,2,3,4-tetrahydro-quinoline-2-acetic acid, ether splitting by means of HBr/acetic acid, reaction into the chloride, Rosenmund reduction to give 1-acetyl-4-oxo-5-hydroxy-1,2,3,4-tetrahydro-quinoline-2-acetaldehyde, condensation with 2-phenyl-2-thiazolin-5-one to give 2-phenyl-4-[2-(1-acetyl-4-oxo-5-hydroxy-1,2,3,4-tetrahydro-2-quinolyl)-ethylidene]-2-thiazolin-5-one, condensation with acetonedicarboxylic acid monomethyl ester-monoamide to give 4-thiobenzamido-1,4,4a,5,5a,6,11,12-octahydro-3,10,12-trihydroxy-6-acetyl-1,11-dioxo-6-aza-naphthacene-2-carboxamide (mixture of stereoisomers), epimerization with pyridine to give 4-de-dimethylamino-4-thiobenzamido-6-acetyl-12a-de-hydroxy-6-aza-tetracycline and hydroxylation.

Workup

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Sources & evidence

ORD record
ord-8f8b049f3ec44368a76add33a07c7274
Source dataset
uspto-grants-1977_05
Patent number
US04024272

Reaction notes

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