Methyl 3-mercaptopropionate → HCID 68708378, compound

HRID 1809658Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:29][C:30]2[C:31]([CH2:36][CH3:37])=[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:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42]>>[CH2:36]([C:31]1[C:30]([O:29][C:4]2[C:5]([NH:8][C:9]3[S:13][N:12]=[C:11]([CH:14]4[CH2:20][CH:19]5[N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]([CH2:17][CH2:18]5)[CH2:15]4)[N:10]=3)=[N:6][CH:7]=[C:2]([S:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])[CH:3]=2)=[CH:35][CH:34]=[CH:33][N:32]=1)[CH3:37]

Participants

Reactant 2

HCID 18050Methyl 3-mercaptopropionate

HCID 67487494HCID 67487494, compound

Product 1

HCID 68708378HCID 68708378, compoundYield 89.8%

Procedure

Following the procedure in Example 52, tert-butyl 3-(5-(5-bromo-3-(2-ethylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (120 mg, 0.2042 mmol) and methyl 3-mercaptopropanoate (24.34 μL, 0.2247 mmol) afforded tert-butyl 3-(5-(3-(2-ethylpyridin-3-yloxy)-5-(3-methoxy-3-oxopropylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (115 mg, 0.183 mmol, 89.8% yield).

Sources & evidence

ORD record: ord-5f13aa64ec1c4bac9891e5d5fb5c1256
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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