(R)-4-((4-(Dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamide → 4-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-(dimethylamino)-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)benzamide

HRID 1476278Notes

Reaction equation

HRID 1476278 reaction equation
[Si:1]([O:8][C@@H:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:38][N:39]([CH3:65])[CH2:40][CH2:41][C@@H:42]([NH:51][C:52]1[CH:57]=[CH:56][C:55]([S:58]([NH2:61])(=[O:60])=[O:59])=[CH:54][C:53]=1[N+:62]([O-:64])=[O:63])[CH2:43][S:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[Si:1]([O:8][C@@H:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:61][S:58]([C:55]3[CH:56]=[CH:57][C:52]([NH:51][C@H:42]([CH2:41][CH2:40][N:39]([CH3:38])[CH3:65])[CH2:43][S:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[C:53]([N+:62]([O-:64])=[O:63])[CH:54]=3)(=[O:59])=[O:60])=[O:22])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 11502754(R)-4-((4-(Dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamide2×HCID 58080201(R)-4-(4-((tert-Butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid2×

Product 1

HCID 866618694-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-(dimethylamino)-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)benzamideYield 36.7%

Procedure

The title product (162.8 mg, yield: 32%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 32 utilizing (R)-4-(4-((tert-butyldimethylsilyloxy)(4 ′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid (INTERMEDIATE 13, 249.6 mg, 0.47 mmol) and (R)-4-(4-(dimethylamino)-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamide (INTERMEDIATE 19, 208.8 mg, 0.49 mmol). The title product was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→10% MeOH/DCM).

Workup

  1. customThe title product was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→10% MeOH/DCM)

Sources & evidence

ORD record
ord-7332a3c0e13b4dd5a7211cb08efcbb13
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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