Diisopropylethylamine → (1S,2S,5R)-2-[3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione

HRID 425806Notes

Reaction equation

HRID 425806 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[C:5]([C:7]([OH:9])=O)[N:6]=1.[F:17][C:18]1([F:38])[CH2:25][C@H:24]2[C@H:20]([CH2:21][NH:22][C@@H:23]2[CH2:26][N:27]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:37])[CH2:19]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[C:5]([C:7]([N:22]2[CH2:21][C@H:20]3[C@H:24]([CH2:25][C:18]([F:17])([F:38])[CH2:19]3)[C@H:23]2[CH2:26][N:27]2[C:28](=[O:37])[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]2=[O:36])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 532718162-Methyl-5-m-tolyl-thiazole-4-carboxylic acidHCID 66703949(1S,2S,5R)-2-(7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 66703707(1S,2S,5R)-2-[3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dioneYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-5-m-tolyl-thiazole-4-carboxylic acid (208 mg), (1S,2S,5R)-2-(7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione (273 mg), DIPEA (0.41 mL) in dry DMF (6 mL) was stirred at RT for 4 h. The reaction mixture was directly purified by preparative HPLC to give the title compound (130 mg, 28%) as an oil. LC-MS: tR=1.02 min; [M+H]+=521.99

Workup

  1. customThe reaction mixture was directly purified by preparative HPLC

Sources & evidence

ORD record
ord-92f4f25eb9094e7c8b36a8f41fbbb856
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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