4-[[(1R)-3-(4-Morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide → 4-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

HRID 1476309Notes

Reaction equation

HRID 1476309 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].[O:38]1[CH2:43][CH2:42][N:41]([CH2:44][CH2:45][C@@H:46]([NH:55][C:56]2[CH:61]=[CH:60][C:59]([S:62]([NH2:65])(=[O:64])=[O:63])=[CH:58][C:57]=2[S:66]([C:69]([F:72])([F:71])[F:70])(=[O:68])=[O:67])[CH2:47][S:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:40][CH2:39]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[CH2:11][CH2:12][N:13]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([NH:65][S:62]([C:59]3[CH:60]=[CH:61][C:56]([NH:55][C@H:46]([CH2:45][CH2:44][N:41]4[CH2:42][CH2:43][O:38][CH2:39][CH2:40]4)[CH2:47][S:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)=[C:57]([S:66]([C:69]([F:71])([F:72])[F:70])(=[O:68])=[O:67])[CH:58]=3)(=[O:63])=[O:64])=[O:22])=[CH:23][CH:24]=2)[CH2:14][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 250584544-[[(1R)-3-(4-Morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide2×HCID 58080201(R)-4-(4-((tert-Butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid2×

Product 1

HCID 866618764-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamideYield 33.3%

Procedure

The title product (71.4 mg, yield: 33%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 33. (R)-4-(4-((tert-Butyldimethylsilyloxy)(4′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid (INTERMEDIATE 13, 106.7 mg, 0.2 mmol) and (R)-4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide (INTERMEDIATE 69, 117 mg, 0.21 mmol) were used as starting materials. The resulting product was purified by column chromatography (ISCO, 4 g silica gel column, eluting with 0→100% EtOAc/hexanes), providing the title product.

Workup

  1. customThe resulting product was purified by column chromatography (ISCO, 4 g silica gel column, eluting with 0→100% EtOAc/hexanes)
  2. customproviding the title product

Sources & evidence

ORD record
ord-6d4fce8f979a47c0a3720358e49bd5ea
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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