1,1'-Thiocarbonyldi-2(1H)-pyridone → Methyl 2-(4-(4'-(2-(cyclobutanecarbonyl) hydrazinecarbothioamido) biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881726Notes

Reaction equation

HRID 881726 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25][CH3:26])=[O:24])([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:27](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:28].[CH:43]1([C:47]([NH:49][NH2:50])=[O:48])[CH2:46][CH2:45][CH2:44]1>O>[CH:43]1([C:47]([NH:49][NH:50][C:27](=[S:28])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[CH:10][C:11]([C:14]45[CH2:19][CH2:18][C:17]([CH2:22][C:23]([O:25][CH3:26])=[O:24])([CH2:20][CH2:21]4)[O:16][CH2:15]5)=[CH:12][CH:13]=3)=[CH:6][CH:7]=2)=[O:48])[CH2:46][CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 969366CyclobutanecarbohydrazideHCID 86700832Methyl 2-(4-(4'-aminobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Product 1

HCID 86700833Methyl 2-(4-(4'-(2-(cyclobutanecarbonyl) hydrazinecarbothioamido) biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared analogous to Example 4, Step 2, starting from methyl 2-(4-(4′-aminobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (500 mg, 1.48 mmol) with 1,1′-thiocarbonyldipyridin-2(1H)-one (379 mg, 1.63 mmol) and cyclobutanecarbohydrazide (254 mg, 2.22 mmol). Water titration of the crude residue affords the title compound as off-white solid after drying (696 mg, 93% yield). LC/MS, ESI-MS(+): 508.4, RT: 1.29 (Condition E).

Workup

  1. customThe title compound was prepared analogous to Example 4, Step 2

Sources & evidence

ORD record
ord-74e899561f964c3fb6feb892b0ff53d3
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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