(R)-4-(4-((tert-Butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid → 4-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-((R)-3-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

HRID 1771217Notes

Reaction equation

HRID 1771217 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](O)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](O[C@@H](C1C=C(Cl)C=CC=1C1C=CC=CC=1)C1CCN(C2C=CC(C(O)=O)=CC=2)CC1)(C(C)(C)C)(C)C.[CH2:75]([N:77]([CH2:80][C@H:81]1[N:86]([CH2:87][CH2:88][C@@H:89]([NH:98][C:99]2[CH:104]=[CH:103][C:102]([S:105]([NH2:108])(=[O:107])=[O:106])=[CH:101][C:100]=2[S:109]([C:112]([F:115])([F:114])[F:113])(=[O:111])=[O:110])[CH2:90][S:91][C:92]2[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=2)[CH2:85][CH2:84][O:83][CH2:82]1)[CH2:78][CH3:79])[CH3:76]>>[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:108][S:105]([C:102]3[CH:103]=[CH:104][C:99]([NH:98][C@H:89]([CH2:88][CH2:87][N:86]4[CH2:85][CH2:84][O:83][CH2:82][C@H:81]4[CH2:80][N:77]([CH2:78][CH3:79])[CH2:75][CH3:76])[CH2:90][S:91][C:92]4[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=4)=[C:100]([S:109]([C:112]([F:113])([F:115])[F:114])(=[O:111])=[O:110])[CH:101]=3)(=[O:106])=[O:107])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 58080201(R)-4-(4-((tert-Butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acidHCID 66723720(R)-4-(4-((tert-butyldimethylsilyloxy)(4-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acidHCID 667239524-((R)-4-((R)-3-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide2×

Product 1

HCID 866618774-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-((R)-3-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamideYield 55%

Procedure

The title product (100 mg, yield: 55%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 89. (R)-4-(4-((tert-Butyldimethylsilyloxy)(4′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid, (INTERMEDIATE 13, 84 mg, 0.16 mmol) and 4-((R)-4-((R)-3-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide (INTERMEDIATE 92, 100 mg, 0.16 mmol) were used as starting materials. The resulting product was purified by column chromatography (ISCO, eluting with 0→20% MeOH/DCM for 19 minutes), providing the title product.

Workup

  1. customThe resulting product was purified by column chromatography (ISCO, eluting with 0→20% MeOH/DCM for 19 minutes)
  2. customproviding the title product

Sources & evidence

ORD record
ord-ab0a1204882b4b118a6002675039b544
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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