Benzoic Acid → HCID 178476374, compound

HRID 1296795Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of acetic acid 2-[4-oxo-4,5-dihydro-thiazol-2-ylamino]-2-(R)-phenyl-ethyl ester (400 mg, 1.43 mmol) and 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (77.3 mg, 0.53 mmol) in toluene (5 mL) in a microwave tube was added benzoic acid (17.64 mg, 0.144 mmol) and piperidine (14.5 uL, 0.144 mmol) at room temperature. The microwave tube was sealed and heated to 150° C. in a closed microwave for 1 h. Then, the mixture was cooled to room temperature and diluted with toluene. The solids were collected by filtration and washed with toluene and dichloromethane. After drying in air, 313 mg (53.6% yield) of acetic acid 2-[4-oxo-5-(1H-pyrrolo[2,3,b]pyridine-3-ylmethylene)-4,5-dihydro-thiazol-2-ylamino]-2-(R)-phenyl-ethyl ester was isolated as a white solid: mp 243.7-246.8° C.; HRES(+) m/e calcd for C21H18N4O3S (M+H)+ 407.1173. found 407.1172.

Workup

customThe microwave tube was sealed
temperatureThen, the mixture was cooled to room temperature
filtrationThe solids were collected by filtration
washwashed with toluene and dichloromethane
customAfter drying in air

Sources & evidence

ORD record: ord-d51e22722a264f3995f0e76fe10ad994
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247727B2

Reaction notes

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