Diisopropylethylamine → HCID 66998520, compound

HRID 560531Notes

Reaction equation

HRID 560531 reaction equation
[NH2:1][CH2:2][C@H:3]1[N:8]([C:9]([C:11]2[N:12]=[C:13]([CH3:23])[S:14][C:15]=2[C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)=[O:10])[CH2:7][C@H:6]2[C@@H:4]1[CH2:5]2.CCN(C(C)C)C(C)C.[Cl:33][C:34]1[S:35][C:36]2[C:37](=[C:39]([C:43](Cl)=[O:44])[CH:40]=[CH:41][CH:42]=2)[N:38]=1>CC#N>[CH3:23][C:13]1[S:14][C:15]([C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)=[C:11]([C:9]([N:8]2[CH2:7][C@H:6]3[C@H:4]([CH2:5]3)[C@H:3]2[CH2:2][NH:1][C:43]([C:39]2[CH:40]=[CH:41][CH:42]=[C:36]3[S:35][C:34]([Cl:33])=[N:38][C:37]=23)=[O:44])=[O:10])[N:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 189844482-Chloro-1,3-benzothiazole-4-carbonyl chlorideHCID 66998654((1S,2S,5R)-2-Aminomethyl-3-aza-bicyclo[3.1.0]hex-3-yl)-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

Product 1

HCID 66998520HCID 66998520, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ((1S,2S,5R)-2-Aminomethyl-3-aza-bicyclo[3.1.0]hex-3-yl)-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone (0.24 mmol) in MeCN (1.0 mL) is treated successively with DIPEA (0.49 mmol) and 2-Chloro-benzothiazole-4-carbonyl chloride (0.24 mmol; U.S. Pat. No. 3,654,296). The mixture is stirred for 30 min and purified by prep. HPLC to give the desired amide. LC-MS: tR=1.03 min; [M+H]+=523.0.

Workup

  1. custompurified by prep

Sources & evidence

ORD record
ord-818eab63cc5b4cb8826068a642dddb56
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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