2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide → 2-[4-[2-(oxazolo[4,5-b]pyridin-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-6-methylpyridin-3-yl]acetamide

HRID 348571Notes

Reaction equation

HRID 348571 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]([N:50]3[CH2:54][CH2:53][CH2:52][CH2:51]3)=[N:40][C:41]([CH3:49])=[CH:42][C:43]=2[N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)=[O:36])[CH2:30][CH2:29]1.SC1NC2C=CC=CC=2N=1.[SH:65][C:66]1[O:67][C:68]2[C:69]([N:74]=1)=[N:70][CH:71]=[CH:72][CH:73]=2>>[O:67]1[C:68]2[C:69](=[N:70][CH:71]=[CH:72][CH:73]=2)[N:74]=[C:66]1[S:65][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][N:31]([CH2:34][C:35]([NH:37][C:38]2[C:39]([N:50]3[CH2:51][CH2:52][CH2:53][CH2:54]3)=[N:40][C:41]([CH3:49])=[CH:42][C:43]=2[N:44]2[CH2:45][CH2:46][CH2:47][CH2:48]2)=[O:36])[CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 116892402-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamideHCID 210873432-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-6-methylpyridin-3-yl]acetamideHCID 178527775HCID 178527775, compoundHCID 178527820HCID 178527820, compound

Product 1

HCID 210873472-[4-[2-(oxazolo[4,5-b]pyridin-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-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(pyrrolidin-1-yl)-6-methylpyridin-3-yl]acetamide, and 2-mercaptobenzimidazole was replaced by 2-mercaptooxazolo[4,5-b]pyridine, to thereby yield the title compound as a pale yellow oil.

Workup

  1. customThe reaction and treatments of Example 12

Sources & evidence

ORD record
ord-058377a086dd4162a51bb76bbb0bf9a8
Source dataset
uspto-grants-2007_02
Patent number
US07176306B2

Reaction notes

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