Acetic Acid → N-(5-Morpholin-4-yl-quinolin-8-yl)-benzenesulfonamide

HRID 513816Notes

Reaction equation

HRID 513816 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[N:22]1([C:15]2[CH:14]=[CH:13][C:12]([NH:11][S:8]([C:3]3[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=3)(=[O:9])=[O:10])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[N:20]3)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681834362-Amino-N-(5-morpholin-4-yl-quinolin-8-yl)-benzenesulfonamide

Product 1

HCID 68183078N-(5-Morpholin-4-yl-quinolin-8-yl)-benzenesulfonamideYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 20 general procedure 36, 2-amino-N-(5-morpholin-4-yl-quinolin-8-yl)-benzenesulfonamide 583 (150 mg, 0.39 mmol), tert-butyl nitrite (79.53 μl, 0.66 mmol), AcOH (1.5 ml) and THF (3 ml) gave the title compound (10 mg, 7%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-85b1e7fd8c6a421ead512f965adbc488
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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