2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid → 4-[(2,3-dihydro-benzo[1,4]dioxine-5-carbonyl)-amino]-1H-pyrazole-3-carboxylic acid

HRID 1012099Notes

Reaction equation

HRID 1012099 reaction equation
F[C:2]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]([OH:14])=[O:13])=[N:9][NH:10][CH:11]=1)=[O:5].[O:20]1C2C=CC=C(C(O)=O)C=2[O:23][CH2:22][CH2:21]1>>[O:20]1[C:16]2[CH:17]=[CH:18][CH:2]=[C:3]([C:4]([NH:6][C:7]3[C:8]([C:12]([OH:14])=[O:13])=[N:9][NH:10][CH:11]=3)=[O:5])[C:15]=2[O:23][CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 781842,3-Dihydro-1,4-benzodioxin-5-carboxylic acidHCID 178524954HCID 178524954, compound

Product 1

HCID 1785224494-[(2,3-dihydro-benzo[1,4]dioxine-5-carbonyl)-amino]-1H-pyrazole-3-carboxylic acid

Procedure

The compound was prepared in a manner analogous to 4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (Example 16D), but using 2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid as the starting acid to give 4-[(2,3-dihydro-benzo[1,4]dioxine-5-carbonyl)-amino]-1H-pyrazole-3-carboxylic acid (340 mg) as a white solid. (1H NMR (300 MHz, DMSO-d6) δ 13.5 (s, 2H), 11.2 (s, 1H), 8.4 (s, 1H), 7.7 (d, 1H), 7.1 (d, 1H), 7.0 (t, 1H), 4.5 (s, 2H), 4.4 (s, 2H)).

Sources & evidence

ORD record
ord-fb7b9023deee4e989e2c23f71af5a9ea
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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