Benzoic Acid → HCID 178467451, compound

HRID 1783636Notes

Reaction equation

[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][CH2:8][C:9](=[O:11])[N:10]=1.[CH2:16]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH:29]=O)[CH:27]=2)[N:22]=[C:21]([NH:31][CH3:32])[N:20]=1)[CH3:17].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:29][C:26]2[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[N:22]=[C:21]([NH:31][CH3:32])[N:20]=[C:19]3[O:18][CH2:16][CH3:17])[C:9](=[O:11])[N:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-(2-chloro-benzylamino)-thiazol-4-one (example 13a, 38.5. 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 2-(2-chloro-benzylamino)-5-(4-ethoxy-2-methylamino-quinazolin-6-ylmethylene)-thiazol-4-one as a brown solid: 43.2 mg (59.5%), MS: m/e 454 (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-d6e2ca4977c14602ad60670b8cba3b6b
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501428B2

Reaction notes

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