Diisopropylethylamine → HCID 57725464, compound

HRID 1988425Notes

Reaction equation

HRID 1988425 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:23]=[CH:22][C:15]3[N:16]=[C:17](S(C)=O)[S:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].Cl.[NH2:25][C@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]1[OH:32].C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[OH:32][C@H:27]1[CH2:28][CH2:29][CH2:30][CH2:31][C@@H:26]1[NH:25][C:17]1[S:18][C:14]2[CH:13]=[C:12]([O:11][C:9]3[CH:8]=[CH:7][N:6]=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:10]=3)[CH:23]=[CH:22][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11715205(1S,2S)-2-Aminocyclohexanol hydrochlorideHCID 577253932-Pyridinecarboxamide, N-methyl-4-[[2-(methylsulfinyl)-6-benzothiazolyl]oxy]-

Product 1

HCID 57725464HCID 57725464, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To the solution of 4-(2-methanesulfinyl-benzothiazol-6-yloxy)-pyridine-2-carboxylic acid methylamide (70 mg, 0.202 mmol, 1.0 eq) in DMA (600 μL), was added (1S,2S)-2-aminocyclohexanol hydrochloride (92 mg, 0.606 mmol, 3.0 eq) followed by diisopropylethylamine (0.21 mL, 1.21 mmol). The reaction was heated at 110° C. for 24-hours. The neat reaction mixture was purified on reverse phase preparatory HPLC. Pure fractions were lyophilized as TFA salts. M+H=398

Workup

  1. customThe neat reaction mixture was purified on reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-77096d7b94de438eab054f84383ec604
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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