Benzenesulfonamide, 3-amino- → HCID 86729562, compound

HRID 2280576Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C:16]1[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.CN(C([O:33][N:34]1[N:42]=[N:41][C:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[S:22]([C:18]1[CH:17]=[C:16]([NH:15][C:12]([C:11]2[C:2]([O:33][N:34]3[C:35]4=[N:40][CH:39]=[CH:38][CH:37]=[C:36]4[N:41]=[N:42]3)=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:14])[CH:21]=[CH:20][CH:19]=1)(=[O:23])(=[O:24])[NH2:25]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Chloroquinoline-3-carboxylic acid (250 mg, 1.20 mmol), 3-aminobenzenesulfonamide (207.3 mg, 1.20 mmol) and HATU (457.8 mg, 1.20 mmol) were combined in DMF (2.5 mL) and treated with 4-methylmorpholine (397.1 μL, 3.61 mmol). The reaction was heated at 60° C. for 12 hours. The reaction was cooled to 25° C. The precipitate was filtered to yield N-(3-sulfamoylphenyl)-2-(triazolo[4,5-b]pyridin-3-yloxy)quinoline-3-carboxamide as a solid. ESI-MS m/z calc. 461.09, found 461.3 (M+1)+; Retention time: 1.35 minutes (3 minutes run).

Workup

temperatureThe reaction was cooled to 25° C
filtrationThe precipitate was filtered

Sources & evidence

ORD record: ord-73b9db87ee444376a9b291603b52f0a8
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139529B2

Reaction notes

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