Acetone → HCID 69689811, compound

HRID 1699620Notes

Reaction equation

[K:1].[C:2]1([S:8]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[CH:14]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].CO.CC(C)=O>[Pd].O>[K:1].[C:2]1([S:8]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:26][CH:25]=3)[CH:14]=2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 35 °C

Procedure

5% Palladium/carbon (0.64 g) is added to a mixture of N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-nitrobenzamide potassium salt (4.27 g), 20% potassium bicarbonate aqueous solution (10.7 g), and methanol (200 ml). The solution is then stirred for 14 hours at 35° C. under a hydrogen environment. The precipitated crystals are dissolved when a mixture solution of acetone and water (acetone/water=5/2, 400 ml) is added and its solids are separated through filtration. The filtrate is concentrated, the precipitated crystals are separated through filtration and dried, and thus, N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide potassium salt (3.15 g) is obtained. 1H-NMR (DMSO-d6, δ): 4.31 (2H, d, J=5.7 Hz), 4.85 (2H, s), 4.91 (1H, br t, J=5.7 Hz), 6.45 (1H, d, J=7.9 Hz), 7.07 (1H, s), 7.13 (1H, d, J=7.9 Hz), 7.29-7.36 (4H, m), 7.43-7.47 (4H, m), 7.60 (2H, d, J=8.1 Hz), 7.65 (2H, d, J=7.6 Hz), 7.73-7.76 (2H, m).

Workup

additionis added
customits solids are separated through filtration
concentrationThe filtrate is concentrated
customthe precipitated crystals are separated through filtration
customdried

Sources & evidence

ORD record: ord-31685a0eb48c482289b15c84f33c0ee7
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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