Sodium Hydroxide → 7-Methoxy-4-phenyl-thiazolo[5,4-c]pyridin-2-ylamine

HRID 917463Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]2[N:17]=[C:16]([NH:18]C(=O)C3C=CC=CC=3)[S:15][C:5]=2[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:4]2[N:17]=[C:16]([NH2:18])[S:15][C:5]=2[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred suspension of 360 mg (1.00 mmol) N-(7-methoxy-4-phenyl-thiazolo[5,4-c]pyridin-2-yl)-benzamide in 3 ml methanol was added 1 ml 5 N aq. sodium hydroxide solution and the resulting solution was then heated at 130° C. for 10 min in a microwave oven. The reaction mixture was then cooled to room temperature and concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 122 mg (48%) 7-methoxy-4-phenyl-thiazolo[5,4-c]pyridin-2-ylamine as a white crystalline solid. ES-MS m/e (%): 258 (M+H+, 100).

Workup

temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bc644e8e6f614a92a09ae4e3a5d99191
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273865B2

Reaction notes

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