Hydrochloric Acid → HCID 86661899, compound

HRID 1771247Notes

Reaction equation

HRID 1771247 reaction equation
[Si]([O:8][C@@H:9]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=1[C:71]1[CH:76]=[CH:75][C:74]([Cl:77])=[CH:73][CH:72]=1)[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:64]=[CH:63][C:19]([C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][C@H:33]([CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][O:47][CH:46]([CH2:50][N:51]([CH2:54][CH3:55])[CH2:52][CH3:53])[CH2:45]4)[CH2:34][S:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[C:28]([S:56]([C:59]([F:62])([F:61])[F:60])(=[O:58])=[O:57])[CH:27]=3)(=[O:25])=[O:24])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)(C(C)(C)C)(C)C.Cl.CCN(CC)CC>O1CCOCC1.C(Cl)Cl>[Cl:77][C:74]1[CH:75]=[CH:76][C:71]([C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][C:65]=2[C@H:9]([OH:8])[CH:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:22][S:23]([C:26]4[CH:31]=[CH:30][C:29]([NH:32][C@H:33]([CH2:42][CH2:43][N:44]5[CH2:49][CH2:48][O:47][CH:46]([CH2:50][N:51]([CH2:54][CH3:55])[CH2:52][CH3:53])[CH2:45]5)[CH2:34][S:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[C:28]([S:56]([C:59]([F:62])([F:61])[F:60])(=[O:57])=[O:58])[CH:27]=4)(=[O:24])=[O:25])=[O:21])=[CH:63][CH:64]=3)[CH2:14][CH2:15]2)=[CH:72][CH:73]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 86661900HCID 86661900, compound

Product 1

HCID 86661899HCID 86661899, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(4-((R)-(tert-butyldimethylsilyloxy)(4′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((2R)-4-(2-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide, single diastereomer (INTERMEDIATE 117, 199 mg, 0.17 mmol) in dioxane (2.027 ml) was added drop wise HCl (4M in dioxane, 0.430 ml, 1.72 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was neutralized with Et3N (2 ml), diluted with DCM and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (ISCO, eluting with 0→100% DCM to 10% MeOH/0.1% NH3 in DCM) to provide the title product as a substantially separated diastereomer (0.06 g, 30%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by column chromatography (ISCO, eluting with 0→100% DCM to 10% MeOH/0.1% NH3 in DCM)

Sources & evidence

ORD record
ord-41ccb17096484a88b5c63771fe70b8d7
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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