Sodium Hydroxide → 7-Methoxy-4-(tetrahydro-pyran-4-yl)thiazolo[5,4-c]pyridin-2-ylamine

HRID 917476Notes

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]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]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]([CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred suspension of 314 mg (0.85 mmol) N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide in 2.5 ml methanol was added 0.85 ml 5 N aq. sodium hydroxide solution and the resulting solution was then heated at 130° C. for 12 min in a microwave oven. The reaction mixture was then cooled to room temperature and partitioned between tetrahydrofuran and 1 N aq. sodium hydroxide solution. The phases were separated and the organic phase was dried over sodium sulfate and concentrated in vacuo. Flash chromatography (methanol/dichloromethane) afforded 174 mg (77%) 7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-ylamine as a light yellow crystalline solid. ES-MS m/e (%): 266 (M+H+, 100).

Workup

temperatureThe reaction mixture was then cooled to room temperature
custompartitioned between tetrahydrofuran and 1 N aq. sodium hydroxide solution
customThe phases were separated
dry with materialthe organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2987292ba131407cb468107536d0b4ec
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273865B2

Reaction notes

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