Hydrochloric Acid → HCID 178503111, compound

HRID 2173920Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C:11]([NH:35]S(C(C)(C)C)=O)([C:13]3[C:21]([S:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]4[C:14]=3[CH:15]=[CH:16][N:17]4[S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH3:12])[N:8](COCC[Si](C)(C)C)[C:7]=2[CH:50]=1)#[N:2].C(C1C=CC2N(COCC[Si](C)(C)C)C(C(NS(C(C)(C)C)=O)(C3C(SC)=CC(C)=C4C=3C=CN4S(C3C=CC(C)=CC=3)(=O)=O)C)=NC=2C=1)#N.Cl.CO>>[NH2:35][C:11]([C:9]1[NH:10][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:50][C:7]=2[N:8]=1)([C:13]1[C:21]([S:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]2[C:14]=1[CH:15]=[CH:16][N:17]2[S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=1)(=[O:27])=[O:26])[CH3:12]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 86701464HCID 86701464, compound

HCID 86701465HCID 86701465, compound

Product 1

HCID 178503111HCID 178503111, compound

Conditions

Temperature: 60 °C

Procedure

To a mixture of (±)-N-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-2-methylpropane-2-sulfinamide and (±)-N-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-2-methylpropane-2-sulfinamide (0.63 g, 0.840 mmol), was added 1.25 M HCl in MeOH (14.00 mL, 16.80 mmol) and the reaction mixture was then heated to 60° C. for 2 h. The reaction mixture was then evaporated directly, basified with ammonium hydroxide and directly loaded onto silica gel and purified by FCC and eluted with heptane/EtOAc 1:1 to give the title compound. MS (ESI−) m/z 514.2 (M−1).

Workup

customThe reaction mixture was then evaporated directly
custompurified by FCC
washeluted with heptane/EtOAc 1:1

Sources & evidence

ORD record: ord-ee0ed7bd4c7248ee8a99dd04b731a8ff
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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