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6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458710, compound

HRID 968717
Notes
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Reaction equation

HRID 968717 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[S:9][CH2:10][C:11](=[O:13])[N:12]=1.C(O[Na])(C)=O.[CH:19]([C:21]1[N:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][C:25]([C:31]#[N:32])=[C:24]2[O:33][CH:34]([CH3:36])[CH3:35])=O>CC(O)=O>[CH:34]([O:33][C:24]1[C:23]2[C:28](=[CH:29][CH:30]=[C:21]([CH:19]=[C:10]3[S:9][C:8]([NH:7][CH2:6][C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[N:12][C:11]3=[O:13])[N:22]=2)[N:27]=[CH:26][C:25]=1[C:31]#[N:32])([CH3:36])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247, compoundHCID 178516942HCID 178516942, compound

Product 1

HCID 178458710HCID 178458710, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one (34.0 mg, 0.16 mmol, (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (57.9 mg, 0.24 mmol) (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 80° C. (oil bath) for 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. The solid was then suspended in AcOEt (20 mL) and filtered. The solid was washed with AcOEt and dried to give 4-isopropoxy-6-{4-oxo-2-[(thiophen-2-ylmethyl)-amino]-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (35.4 mg, 50.8%). HR-ES (+) m/e calcd for C21H17N5O2S2 (M+H)+ 436.0897. found 436.0895.

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
  5. filtrationfiltered
  6. washThe solid was washed with AcOEt
  7. customdried

Sources & evidence

ORD record
ord-d4ce85bc08af42538acb3aeea76f94d5
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