6-fluoro-1H-benzimidazole-2-thiol → 2-[4-[2-(5-fluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

HRID 227523Notes

Reaction equation

HRID 227523 reaction equation
OCCN1CCN(CC(NC2C(SC)=NC(C)=CC=2SC)=O)CC1.O[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]([NH:37][C:38]2[C:39]([O:51][CH2:52][C:53]([F:56])([F:55])[F:54])=[N:40][C:41]([CH3:50])=[CH:42][C:43]=2[O:44][CH2:45][C:46]([F:49])([F:48])[F:47])=[O:36])[CH2:30][CH2:29]1.SC1NC2C=CC=CC=2N=1.[F:67][C:68]1[CH:77]=[CH:76][C:71]2[N:72]=[C:73]([SH:75])[NH:74][C:70]=2[CH:69]=1>>[F:67][C:68]1[CH:77]=[CH:76][C:71]2[N:72]=[C:73]([S:75][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][N:31]([CH2:34][C:35]([NH:37][C:38]4[C:39]([O:51][CH2:52][C:53]([F:56])([F:55])[F:54])=[N:40][C:41]([CH3:50])=[CH:42][C:43]=4[O:44][CH2:45][C:46]([F:48])([F:49])[F:47])=[O:36])[CH2:32][CH2:33]3)[NH:74][C:70]=2[CH:69]=1

Participants

5

Reactant 4

HCID 34348856-fluoro-1H-benzimidazole-2-thiolHCID 116892402-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamideHCID 231109552-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4 bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamideHCID 178527775HCID 178527775, compound

Product 1

HCID 231161592-[4-[2-(5-fluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

Procedure

The reaction and treatments of Example 12 were repeated, except that 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide was replaced by 2-[4-(2-hydroxyethyl) piperazin-1-yl]-N-[2, 4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide, and 2-mercaptobenzimidazole was replaced by 5-fluoro-2-mercaptobenzimidazole, to thereby yield the title compound as a pale brown foamed substance.

Workup

  1. customThe reaction and treatments of Example 12

Sources & evidence

ORD record
ord-5745e515fa364429b404e8a4a5335569
Source dataset
uspto-grants-2009_07
Patent number
US07560547B2

Reaction notes

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