Methyl Thioglycolate → HCID 68705417, compound

HRID 1809624Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:29][C:30]2[C:31]([CH3:36])=[N:32][CH:33]=[CH:34][CH:35]=2)[C:5]([NH:8][C:9]2[S:13][N:12]=[C:11]([CH:14]3[CH2:20][CH:19]4[N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]([CH2:17][CH2:18]4)[CH2:15]3)[N:10]=2)=[N:6][CH:7]=1.[SH:37][CH2:38][C:39]([O:41][CH3:42])=[O:40]>>[CH3:42][O:41][C:39](=[O:40])[CH2:38][S:37][C:2]1[CH:3]=[C:4]([O:29][C:30]2[C:31]([CH3:36])=[N:32][CH:33]=[CH:34][CH:35]=2)[C:5]([NH:8][C:9]2[S:13][N:12]=[C:11]([CH:14]3[CH2:20][CH:19]4[N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]([CH2:17][CH2:18]4)[CH2:15]3)[N:10]=2)=[N:6][CH:7]=1

Participants

Reactant 2

HCID 16907Methyl Thioglycolate

HCID 67487136HCID 67487136, compound

Product 1

HCID 68705417HCID 68705417, compoundYield 84%

Procedure

Following the procedure in Example 52, tert-butyl 3-(5-(5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (526 mg, 0.917 mmol) and methyl 2-mercaptoacetate (92.3 μL, 1.01 mmol) afforded tert-butyl 3-(5-(5-(2-methoxy-2-oxoethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (461 mg, 0.770 mmol, 83.9% yield).

Sources & evidence

ORD record: ord-9ad76e2608294fb1988da61ac30b1d4d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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