HCID 178418247, compound → HCID 178458599, compound

HRID 968743Notes

Reaction equation

[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[N:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][C:17](C#N)=[C:16]3[O:25][CH:26]([CH3:28])[CH3:27])[C:9](=[O:11])[N:10]=1.C(O[Na])(C)=O.C(OC1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)(C)C>CC(O)=O>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([O:25][CH:26]([CH3:28])[CH3:27])[CH:17]=[CH:18][N:19]=3)[N:14]=2)[C:9](=[O:11])[N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (38.5 mg, 0.16 mmol) (see Example 2), AcONa (160 mg, 1.95 mmol), molecular sieves, and 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (38.9 mg, 0.18 mmol) (see Example 20) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° 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 collected by filtration and washed with water, acetone and ether to give 2-(2-chloro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a brown solid (31.4 mg, 44.7%). HR-ES (+) m/e calcd for C22H19ClN4O2S (M+H)+ 439.0990. found 439.0987.

Workup

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water
filtrationThe solid was collected by filtration
washwashed with water, acetone and ether

Sources & evidence

ORD record: ord-e114255a5b4449fbb2cc310e948eb5bf
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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