Hydrochloric Acid → 4-amino-6-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-hydroxythieno[3,2-b]pyridin-5(4H)-one

HRID 601216Notes

Reaction equation

[OH:1][C:2]1[C:3]2[S:24][CH:23]=[CH:22][C:4]=2[N:5]([N:14]=CC2C=CC=CC=2)[C:6](=[O:13])[C:7]=1[C:8](OCC)=O.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([NH2:35])(=[O:34])=[O:33].[OH-].[K+].Cl>C1(C)C=CC=CC=1>[NH2:14][N:5]1[C:6](=[O:13])[C:7]([C:8]2[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[S:32](=[O:33])(=[O:34])[N:35]=2)=[C:2]([OH:1])[C:3]2[S:24][CH:23]=[CH:22][C:4]1=2

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Example 268C (2.29 g, 6.69 mmol) was reacted with 2-aminobenzenesulfonamide (1.15 g, 6.69 mmol) in toluene (60 mL), and stirred at reflux for 5 hours. The reaction was cooled to 25° C. and the resulting precipitate was collected by filtration and dried (1.95 g, 62%). The resulting solid (1.95 g, 4.2 mmol) was reacted with 10% aqueous KOH (60 mL) at reflux for 24 hours, cooled to 25° C. and acidified with concentrated hydrochloric acid to pH 2. The resulting solid was collected by filtration, washed repeatedly with water and dried to provide the title compound (1.5 g, 98%).(Any sodium salt made?) 1H NMR (300 MHz, DMSO-d6) δ ppm 6.12 (s, 2 H) 7.49 (d, J=5.52 Hz, 1 H) 7.57 (m, 2 H) 7.79 (t, J=7.17 Hz, 1 H) 7.93 (d, J=7.72 Hz, 1 H) 8.34 (d, J=5.52 Hz, 1 H) 14.33 (s, 1 H) 14.68 (s, 1 H).

Workup

temperatureat reflux for 5 hours
filtrationthe resulting precipitate was collected by filtration
customdried (1.95 g, 62%)
temperatureat reflux for 24 hours
temperaturecooled to 25° C.
filtrationThe resulting solid was collected by filtration
washwashed repeatedly with water
customdried

Sources & evidence

ORD record: ord-f4abaaedd2f8432b95df39e97f4f43d1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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