HCID 67178263, compound → HCID 87300297, compound

HRID 1045065Notes

Reaction equation

HRID 1045065 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11](=[O:13])[CH3:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C1CNC(=O)C1.[Br:20][Br-]Br>CO>[Br:20][CH2:12][C:11]([CH:8]1[CH2:9][CH2:10][C:5]2([CH2:1][CH2:2][CH2:3][CH2:4]2)[CH2:6][CH2:7]1)=[O:13]

Participants

3

Reactant 1

HCID 67178263HCID 67178263, compound

Product 1

HCID 87300297HCID 87300297, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Spiro[4.5]dec-8-yl-ethanone (120 mg, 0.66 mmol) was treated with pyrrolidone hydrotribromide (360 mg, 0.72 mmol) in methanol (3 mL) following a method analogous to General Procedure B1 to produce 2-bromo-1-spiro[4.5]dec-8-yl-ethanone (120 mg). This bromo ketone was used without further purification. It was treated with 3-[1-(5-methyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester (158 mg, 0.5 mmol) following a method analogous to General Procedure C to afford 3-[(5-methyl-thiophen-2-ylmethyl)-(4-spiro[4.5]dec-8-yl-thiazol-2-yl)-amino]-propionic acid tert-butyl ester after workup and purification (30 mg).

Sources & evidence

ORD record
ord-7cc12d56644a47418cdd7e5040b7aa06
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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