2H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxide → 4-[(2-Chloro-1,3-thiazol-5-yl)methyl]-6-{1,1-dioxido-7-[(triisopropylsilyl)oxy]-4H-1,2,4-benzothiadiazin-3-yl}-7-hydroxythieno[3,2-b]pyridin-5(4H)-one

Participants

Role	Name	HCID	Charge
Reactant	2H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxide	HCID 658835	—
Reactant	1-butyl-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione	HCID 10398542	—
Reactant	1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dione	HCID 86592151	—
Reactant	Ethyl {1,1-dioxido-7-[(triisopropylsilyl)oxy]-4H-1,2,4-benzothiadiazin-3-yl}acetate	HCID 86592152	—
Product	4-[(2-Chloro-1,3-thiazol-5-yl)methyl]-6-{1,1-dioxido-7-[(triisopropylsilyl)oxy]-4H-1,2,4-benzothiadiazin-3-yl}-7-hydroxythieno[3,2-b]pyridin-5(4H)-one	HCID 136373991	—

Reaction Steps

The title compound was prepared according to the procedure of Example 1D substituting the product of Example 140A for the product of Example 1B and substituting the product of Example 307C for the product of Example 1C (0.29 g, 66%). MS (ESI−) m/z 649 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.09 (d, J=7.35 Hz, 18 H) 1.28 (m, 3 H) 5.63 (s, 2 H) 7.22 (d, J=2.57 Hz, 1 H) 7.31 (dd, J=8.82, 2.94 Hz, 1 H) 7.65 (d, J=8.82 Hz, 1 H) 7.86 (d, J=5.52 Hz, 1 H) 7.95 (s, 1 H) 8.42 (d, J=5.52 Hz, 1 H) 14.05 (s, 1 H) 14.96 (s, 1 H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07902203B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-21dec6eb81a14713be3157ebbc3c3738
Source note	uspto-grants-2011_03