Benzoic Acid → HCID 178467454, compound

HRID 1783645Notes

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.[CH2:14]([O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH:27]=O)[CH:25]=2)[N:20]=[C:19]([NH:29][CH3:30])[N:18]=1)[CH3:15].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:14]([O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH:27]=[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])[CH:25]=2)[N:20]=[C:19]([NH:29][CH3:30])[N:18]=1)[CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one (34.0 mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The reaction mixture was heated to 150° C. with microwave for 30 min. The reaction mixture was then cooled to r.t. and the solid was filtered off, washed with toluene, MeOH and ether to give 5-(4-ethoxy-2-methylamino-quinazolin-6-ylmethylene)-2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one as a brown solid: 48.6 mg (69.1%), MS: m/e 426 (MH+).

Workup

temperatureThe reaction mixture was then cooled to r.t.
filtrationthe solid was filtered off
washwashed with toluene, MeOH and ether

Sources & evidence

ORD record: ord-49f3bc5cad5e43df963509fa7841c881
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501428B2

Reaction notes

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