Benzoic Acid → HCID 178467455, compound

HRID 1783638Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][NH:8][C:9]1[S:10][CH2:11][C:12](=[O:14])[N:13]=1.[CH2:15]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH:28]=O)[CH:26]=2)[N:21]=[C:20]([NH:30][CH3:31])[N:19]=1)[CH3:16].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:15]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH:28]=[C:11]3[S:10][C:9]([NH:8][CH2:7][C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])=[N:13][C:12]3=[O:14])[CH:26]=2)[N:21]=[C:20]([NH:30][CH3:31])[N:19]=1)[CH3:16]

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (36.2. 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 45 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-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one as a brown solid: 56.5 mg (80.4%), MS: m/e 440 (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-eecd9b28c4a9488cac0498959b85a29f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501428B2

Reaction notes

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