Ethanolamine → 2-(3-Quinolylimino)-3,5-diisobutyl-1,3thiazolidine

HRID 276431

Reaction equation

NC1C=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9]C=CC=2.[CH:12]1[CH:17]=[C:16]2[CH:18]=[C:19]([N:22]=[C:23]=[S:24])[CH:20]=[N:21][C:15]2=[CH:14][CH:13]=1.O[CH2:26][C@@H:27](N)[CH2:28][CH:29]([CH3:31])[CH3:30].COC(=O)[C@H](CC(C)C)N.OCCN.CC(C)C[C@H](NCC(C)C)CO.[Cl-].C([NH3+])C(C)C>>[N:21]1[C:15]2[C:16](=[CH:17][CH:12]=[CH:13][CH:14]=2)[CH:18]=[C:19]([N:22]=[C:23]2[N:4]([CH2:5][CH:10]([CH3:11])[CH3:9])[CH2:26][CH:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:24]2)[CH:20]=1

Participants

Reactant 7

HCID 700Ethanolamine

HCID 113753-Aminoquinoline

HCID 21133Isobutylaminehydrochloride2×

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

HCID 137184213-Isothiocyanatoquinoline2×

HCID 22951222(2S)-4-methyl-2-(isobutylamino)pentanol

Product 1

HCID 183163322-(3-Quinolylimino)-3,5-diisobutyl-1,3thiazolidine

Procedure

3-Aminoquinoline was converted to 3-quinoline isothiocyanate according to Method A2c. (1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (2S)-4-methyl-2-(isobutylamino)pentanol as described in Method B4c, Steps 1-2. The alcohol was converted to N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride as described in Method B7c. 3-Quinoline isothiocyanate was reacted with N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride according to Method C1f to give 2-(3-quinolylimino)-3,5-diisobutyl-1,3thiazolidine.

Sources & evidence

ORD record: ord-5ef769350033476a90dd5eeb24076b1d
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

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