N-Methylethylamine → N-ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851765Notes

Reaction equation

F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH2:19]([NH:21][CH3:22])[CH3:20]>O>[CH2:19]([N:21]([CH3:22])[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][N:7]=1)[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

In a microwave vial were added 2-(6-fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole (75 mg, 0.289 mmol), water (2.0 mL) and ethylmethylamine (0.50 mL) and the reaction was heated in a microwave oven at 100° C. for 5 min. The precipitated product was filtered off, washed with water and dried in a desicator over P2O5 to yield the product (70 mg) as a beige solid. 1H NMR δ ppm 8.71 (d, 1 H) 8.06 (dd, 2.53 Hz, 1 H) 7.85 (d, 1 H) 7.66 (d, 1H) 7.08 (dd, 1 H) 6.76 (d, 1 H) 3.84 (s, 3 H) 3.64 (q, 2 H) 3.08 (s, 3 H) 1.12 (t, 3 H); MS m/z (M+H) 300.

Workup

filtrationThe precipitated product was filtered off
washwashed with water
dry with materialdried in a desicator over P2O5

Sources & evidence

ORD record: ord-54fb2256cf3a4f319a0fff9b99c0d6bf
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957215B2

Reaction notes

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