Ammonia → HCID 86681224, compound

HRID 1848251Notes

Reaction equation

I[C:2]1[C:3](=[O:20])[N:4]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]3[N:13]=[C:14]([S:16][CH3:17])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:6][N:7]=1.[NH3:21]>CS(C)=O>[NH2:21][C:2]1[C:3](=[O:20])[N:4]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]3[N:13]=[C:14]([S:16][CH3:17])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred mixture of 3-iodo-1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyrazin-2(1H)-one (750 mg, 1.81 mmol), ammonia (7 M solution in MeOH, 2 mL, 14 mmol), and DMSO (1.5 mL), was heated in a Biotage Microwave Synthesizer at 150° C. for 15 min. The mixture was cooled to and partitioned between EtOAc and a 1:1 mixture of water and brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradient of 100% DCM to 2% MeOH in DCM to afford 3-amino-1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyrazin-2(1H)-one (149 mg) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 7.96 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.43 (dd, J=1.5, 8.4 Hz, 1H), 6.92 (d, J=4.7 Hz, 1H), 6.65-6.67 (br m, 3H), 5.11 (s, 2H), 2.78 (s, 3H); LCMS (ESI) m/z 305 (M+H)+.

Workup

temperatureThe mixture was cooled to and
custompartitioned between EtOAc
additiona 1:1 mixture of water and brine
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel flash chromatography
washeluting with a gradient of 100% DCM to 2% MeOH in DCM

Sources & evidence

ORD record: ord-58134e48c3734287bf98e40c745876ba
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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