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6-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile → HCID 178429645, compound

HRID 968728
Notes
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Reaction equation

HRID 968728 reaction equation
CC1C=CSC=1CNC1SCC(=O)N=1.C(O[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH:29]=[C:30]3[S:34][C:33]([NH:35][CH2:36][C:37]4[S:38][CH:39]=[CH:40][C:41]=4[CH3:42])=[N:32][C:31]3=[O:43])[N:27]=2)[N:22]=[CH:21][C:20]=1[C:44]#[N:45])(C)C.O=C1C(=CC2N=C3C(=CC=2)N=CC(C#N)=C3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[CH3:42][C:41]1[CH:40]=[CH:39][S:38][C:37]=1[CH2:36][NH:35][C:33]1[S:34][C:30](=[CH:29][C:26]2[N:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][C:20]([C:44]#[N:45])=[CH:19]3)[C:31](=[O:43])[N:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1784296466-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrileHCID 178429647HCID 178429647, compoundHCID 178510297HCID 178510297, compound

Product 1

HCID 178429645HCID 178429645, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (21.7 mg, 0.10 mmol), AcONa (160 mg, 1.95 mmol) (see Example 5), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (22.0 mg, 0.12 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 1.5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, AcOEt and ether to give 6-{2-[(3-methyl-thiophen-2-ylmethyl)-amino]-4-oxo-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (14.0 mg, 35.8%). HR-ES (+) m/e calcd for C19H13N5OS2 (M+H)+ 414.0454. found 414.0452.

Workup

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water, AcOEt and ether

Sources & evidence

ORD record
ord-9c409334352143518122fe0675cb3c19
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07304074B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes