Methylamine → HCID 18456580, compound

To a suspension of (2-chloro-4-methoxy-phenyl)-acetic acid (49c) (500 mg, 2.50 mmol) in CH2Cl2 (10 mL) was added 2.0 M oxalyl chloride in CH2Cl2 (3.75 mL, 7.50 mmol), follow by 4 drops of DMF. The mixture was stirred at ambient temperature for one hour, concentrated, and further dried under high vacuum. The residue was re-dissolved in CH2Cl2 (10 mL), to this solution was added 2.0 M methylamine in THF (3.5 mL, 7.50 mmol). After stirring at ambient temperature overnight, the reaction was quenched with water, extracted with CH2Cl2 for three times. The combined organic phase was dried over Na2SO4, and concentrated to give 0.46 g white solid as the intermediate 70a. 1H NMR (300 MHz, CD3OD) δ 7.14 (d, 1H, J=8.66 Hz), 6.87 (d, 1H, J=2.64 Hz), 6.78–6.72 (m, 1H), 3.68 (s, 3H), 3.48 (s, 2H), 2.62 (s, 3H). LCMS (ESI+) [M+H]/z Calc'd 214, found 214.

1. concentrationconcentrated
2. customfurther dried under high vacuum
3. dissolutionThe residue was re-dissolved in CH2Cl2 (10 mL), to this solution
4. stirringAfter stirring at ambient temperature overnight
5. customthe reaction was quenched with water
6. extractionextracted with CH2Cl2 for three times
7. dry with materialThe combined organic phase was dried over Na2SO4
8. concentrationconcentrated

ORD record

ord-2031cf01b9e6429fbec407e5ac08068f

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208500B2