Acetone → Acetoacetic Acid

Participants

Role	Name	HCID	Charge
Reactant	Acetone	HCID 180	—
Reactant	Tert-butyl 4-{4-amino-7-[(1e)-3-(diethylamino)-1-propenyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenylcarbamate	HCID 18451456	—
Solvent	Hydrochloric Acid	HCID 313	—
Product	Acetoacetic Acid	HCID 96	—
Product	3-(4-Amino-3-methoxyphenyl)-7-[(1e)-3-(diethylamino)-1-propenyl]thieno[3,2-c]pyridin-4-amine	HCID 18450708	—

Reaction Steps

A mixture of Example 365B (425 mg, 0.88 mmol) in acetone (10 mL) and 6N aqueous hydrochloric acid (2 mL) was stirred for 18 hours at ambient temperature then concentrated under reduced pressure. The residue was then purified by preparative reverse phase HPLC to provide the desired product as the diacetate salt. 1H NMR (DMSO-d6, 400 MHz) δ 7.89 (s, 1H), 7.39 (s, 1H), 6.82 (s, 1H), 6.73 (s, 2H), 6.20 (m, 1H), 5.65 (br s, 2H), 3.78 (s, 3H), 3.30 (d, 2H), 2.56 (q, 4H), 1.88 (s, 6H), 1.01 (t, 6H); MS m/e 383.4 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07737160B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-367b7d43e9bc41959719091afb7378aa
Source note	uspto-grants-2010_06